NL8302718A - Werkwijze voor de bereiding van een aminolactoncarbonzuur. - Google Patents

Werkwijze voor de bereiding van een aminolactoncarbonzuur. Download PDF

Info

Publication number: NL8302718A
Authority: NL; Netherlands
Prior art keywords: formula; compound; mmol; mixture; benzyl
Prior art date: 1982-07-30

Application number

NL8302718A

Other languages

English (en)

Dutch (nl)

Original Assignee

Richter Gedeon Vegyeszet

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-07-30

Filing date

1983-07-29

Publication date

1984-02-16

1983-07-29 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1984-02-16 Publication of NL8302718A publication Critical patent/NL8302718A/nl

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 9
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 49
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 5
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
SZCTYPPFNNHBOW-UHFFFAOYSA-N 2-[1-benzyl-3-(1-hydroxyethyl)-4-oxoazetidin-2-yl]acetonitrile Chemical compound O=C1C(C(O)C)C(CC#N)N1CC1=CC=CC=C1 SZCTYPPFNNHBOW-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
239000000203 mixture Substances 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
-1 cyanomethyl Chemical group 0.000 description 9
239000005457 ice water Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 4
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 4
239000003463 adsorbent Substances 0.000 description 4
239000003513 alkali Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
UKPNTOUTEWBHSZ-STQMWFEESA-N (3R,4R)-1-benzyl-4-(hydroxymethyl)-3-(2-methyl-1,3-dioxolan-2-yl)azetidin-2-one Chemical compound C(C1=CC=CC=C1)N1C([C@H]([C@@H]1CO)C1(OCCO1)C)=O UKPNTOUTEWBHSZ-STQMWFEESA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 2
GDWNDZIRWGPDDB-UHFFFAOYSA-N 2-(benzylamino)propanedioic acid Chemical class OC(=O)C(C(O)=O)NCC1=CC=CC=C1 GDWNDZIRWGPDDB-UHFFFAOYSA-N 0.000 description 2
QHHOPBFYKJDFJD-UHFFFAOYSA-N 4-(benzylamino)-2-methyl-6-oxooxane-3-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1C(C)OC(=O)CC1NCC1=CC=CC=C1 QHHOPBFYKJDFJD-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
XUQMFHLTFVJATG-UHFFFAOYSA-N diethyl 3-acetyl-1-benzyl-4-oxoazetidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)C(C(C)=O)C(=O)N1CC1=CC=CC=C1 XUQMFHLTFVJATG-UHFFFAOYSA-N 0.000 description 2
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
LPYULLOGIFLAEP-UHFFFAOYSA-N 3-(2-methyl-1,3-dioxolan-2-yl)azetidin-2-one Chemical compound CC1(OCCO1)C1C(NC1)=O LPYULLOGIFLAEP-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
FUOPBUPJYJAIDK-KBPBESRZSA-N C(C1=CC=CC=C1)N1C([C@H]([C@@H]1CC#N)C1(OCCO1)C)=O Chemical compound C(C1=CC=CC=C1)N1C([C@H]([C@@H]1CC#N)C1(OCCO1)C)=O FUOPBUPJYJAIDK-KBPBESRZSA-N 0.000 description 1
LSKKEMWVVMXNDL-STQMWFEESA-N C(C1=CC=CC=C1)N1C([C@H]([C@@H]1CI)C1(OCCO1)C)=O Chemical compound C(C1=CC=CC=C1)N1C([C@H]([C@@H]1CI)C1(OCCO1)C)=O LSKKEMWVVMXNDL-STQMWFEESA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
FHSWCMQZXMMQBI-KBPBESRZSA-N [(2R,3R)-1-benzyl-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidin-2-yl]methyl methanesulfonate Chemical compound C(C1=CC=CC=C1)N1C([C@H]([C@@H]1COS(=O)(=O)C)C1(OCCO1)C)=O FHSWCMQZXMMQBI-KBPBESRZSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
XFMAATAYRYOEPM-UHFFFAOYSA-N diethyl 1-benzyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2,2-dicarboxylate Chemical compound O=C1CC(O)(C)C(C(=O)OCC)(C(=O)OCC)N1CC1=CC=CC=C1 XFMAATAYRYOEPM-UHFFFAOYSA-N 0.000 description 1
BXAHREGKKIIYQA-UHFFFAOYSA-N diethyl 2-(benzylamino)propanedioate;hydrochloride Chemical compound Cl.CCOC(=O)C(C(=O)OCC)NCC1=CC=CC=C1 BXAHREGKKIIYQA-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyrane Compounds (AREA)

NL8302718A 1982-07-30 1983-07-29 Werkwijze voor de bereiding van een aminolactoncarbonzuur. NL8302718A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU822449A HU190404B (en)	1982-07-30	1982-07-30	Process for preparing amino-lactone-carboxylic acid
HU244982		1982-07-30

Publications (1)

Publication Number	Publication Date
NL8302718A true NL8302718A (nl)	1984-02-16

Family

ID=10959417

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8302718A NL8302718A (nl)	1982-07-30	1983-07-29	Werkwijze voor de bereiding van een aminolactoncarbonzuur.

Country Status (13)

Country	Link
US (1)	US4559406A (es)
JP (1)	JPS5984861A (es)
AT (1)	AT380243B (es)
BE (1)	BE897393A (es)
CH (2)	CH655315A5 (es)
DE (1)	DE3327482A1 (es)
ES (1)	ES8505360A1 (es)
FR (2)	FR2546889B1 (es)
GB (1)	GB2124628B (es)
HU (1)	HU190404B (es)
IT (1)	IT1165462B (es)
NL (1)	NL8302718A (es)
PT (1)	PT77127B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8531638D0 (en) *	1985-12-23	1986-02-05	Ici Plc	Chemical compounds
GB8605413D0 (en) *	1986-03-05	1986-04-09	Ici Plc	Chemical compounds
US4992545A (en) *	1989-09-20	1991-02-12	Eli Lilly And Company	Process for preparing 4-substituted azetidinones
US5106475A (en) *	1989-09-20	1992-04-21	Eli Lilly And Company	Process for preparing 4-substituted azetidinones

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GB2003875B (en) *	1977-09-06	1982-01-20	Montedison Spa	Synthesis of unsaturated esters and lactone from butadiene and carbon dioxide
PT71553B (en) *	1979-07-23	1981-12-14	Merck & Co Inc	Process for the preparation of thienamycin and intermediates
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1982
- 1982-07-30 HU HU822449A patent/HU190404B/hu not_active IP Right Cessation
1983
- 1983-06-27 US US06/508,436 patent/US4559406A/en not_active Expired - Fee Related
- 1983-06-29 CH CH3564/83A patent/CH655315A5/de not_active IP Right Cessation
- 1983-06-29 CH CH4917/85A patent/CH658649A5/de not_active IP Right Cessation
- 1983-07-27 AT AT0272483A patent/AT380243B/de not_active IP Right Cessation
- 1983-07-28 BE BE1/10839A patent/BE897393A/fr not_active IP Right Cessation
- 1983-07-29 ES ES524578A patent/ES8505360A1/es not_active Expired
- 1983-07-29 FR FR8312521A patent/FR2546889B1/fr not_active Expired
- 1983-07-29 DE DE19833327482 patent/DE3327482A1/de not_active Withdrawn
- 1983-07-29 IT IT22323/83A patent/IT1165462B/it active
- 1983-07-29 GB GB08320494A patent/GB2124628B/en not_active Expired
- 1983-07-29 NL NL8302718A patent/NL8302718A/nl not_active Application Discontinuation
- 1983-07-29 JP JP58137919A patent/JPS5984861A/ja active Pending
- 1983-07-29 PT PT77127A patent/PT77127B/pt unknown
1984
- 1984-03-23 FR FR8404545A patent/FR2541998B1/fr not_active Expired

Also Published As

Publication number	Publication date
FR2541998A1 (fr)	1984-09-07
FR2546889A1 (fr)	1984-12-07
US4559406A (en)	1985-12-17
ES524578A0 (es)	1985-05-16
ATA272483A (de)	1985-09-15
PT77127B (en)	1986-01-24
CH658649A5 (de)	1986-11-28
IT8322323A0 (it)	1983-07-29
IT1165462B (it)	1987-04-22
FR2546889B1 (fr)	1987-01-16
GB8320494D0 (en)	1983-09-01
GB2124628A (en)	1984-02-22
PT77127A (en)	1983-08-01
HU190404B (en)	1986-09-29
BE897393A (fr)	1984-01-30
AT380243B (de)	1986-04-25
CH655315A5 (de)	1986-04-15
JPS5984861A (ja)	1984-05-16
GB2124628B (en)	1985-12-04
IT8322323A1 (it)	1985-01-29
FR2541998B1 (fr)	1986-02-21
DE3327482A1 (de)	1984-02-02
ES8505360A1 (es)	1985-05-16

Publication	Publication Date	Title
DE3415035A1 (de)	1984-10-25	Verfahren zur stereospezifischen herstellung von diltiazemhydrochlorid
DE3588039T2 (de)	1995-11-16	Azetidinonderivate und Verfahren zu ihrer Herstellung.
JPH0557980B2 (es)	1993-08-25
DE3382761T2 (de)	1995-03-09	Verfahren zur Herstellung von Penem-Verbindungen.
Huffman et al.	1987	Stereoselective total synthesis of (±)-isocelorbicol
DE2740280A1 (de)	1978-03-09	7-acylamino-8-oxo-3-oxa-1-azabicyclo eckige klammer auf 4.2.0 eckige klammer zu octan-2-carbonsaeure-derivate
NL8302718A (nl)	1984-02-16	Werkwijze voor de bereiding van een aminolactoncarbonzuur.
DE3512250A1 (de)	1985-10-17	Anhydropenicillin-zwischenverbindungen und verfahren zu deren herstellung
FR2518098A1 (fr)	1983-06-17	Procede pour la preparation de derives penem optiquement actifs
LU82320A1 (fr)	1980-07-02	Inhibiteurs de b-lactamase et procede pour les preparer
Gunda et al.	1997	2-Amino-1-phenyl-propan-1, 3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones
US5202443A (en)	1993-04-13	Process for preparing 1-(2s)-3-mercapto-methyl-1-oxopropyl)-l-proline
JPH06172376A (ja)	1994-06-21	プシコフラノース及びプシコピラノース誘導体
DE3780730T2 (de)	1993-03-18	Optisch wirksame beta-aminosaeure derivate und ihre salze und verfahren zu deren herstellung.
EP0270481B1 (de)	1991-04-17	Neues Verfahren zur Herstellung von optisch aktiven Carbacyclin-Zwischenprodukten
DE69416117T2 (de)	1999-06-24	Verfahren zur herstellung von kondensierten carbapenemderivaten
CH635057A5 (de)	1983-03-15	Verfahren zur herstellung von tricycloheptan-6-onen.
DE2534601A1 (de)	1977-02-17	Verfahren zur herstellung von camptothecin-aehnlichen verbindungen
US4434099A (en)	1984-02-28	Beta-lactam compounds containing a protected C-acetyl group, process for their preparation and pharmaceutical compositions containing them
KR100241089B1 (ko)	2000-03-02	2-메르캅토-4-메틸-1,3-티아졸-5-아세트산의 신규한제조방법
EP0478803B1 (en)	1996-07-10	Process for producing (S)-gamma-acyloxy-methyl-alpha-beta-butenolide
FI85375C (fi)	1992-04-10	Nytt foerfarande foer framstaellning av apovinkaminolderivat.
AT393838B (de)	1991-12-27	Stereogesteuertes verfahren zur herstellung von neuen penem-verbindungen
CH661269A5 (de)	1987-07-15	Heterocyclische essigsaeureester.
JP2763214B2 (ja)	1998-06-11	Ｌ−プロリン誘導体の製造法

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1989-03-01	BV	The patent application has lapsed