SK14772000A3 - Spôsob výroby derivátov N-(1-kyanoalkyl)-2-fenoxypropiónamidu - Google Patents

Spôsob výroby derivátov N-(1-kyanoalkyl)-2-fenoxypropiónamidu Download PDF

Info

Publication number: SK14772000A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; preparation; mol; toluene
Prior art date: 1998-04-20

Application number

SK1477-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Albert Anthony Cevasco

Kenneth Alfred Martin Kremer

Original Assignee

American Cyanamid Company

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.)

1998-04-20

Filing date

1999-04-05

Publication date

2002-05-09

1999-04-05 Application filed by American Cyanamid Company filed Critical American Cyanamid Company

2002-05-09 Publication of SK14772000A3 publication Critical patent/SK14772000A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 26
238000004519 manufacturing process Methods 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 14
239000000203 mixture Substances 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 8
150000004820 halides Chemical class 0.000 claims abstract description 5
239000006184 cosolvent Substances 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 57
238000002360 preparation method Methods 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
-1 aminonitrile compound Chemical class 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 7
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
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 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims 2
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 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 8
150000001412 amines Chemical class 0.000 abstract description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
239000000047 product Substances 0.000 description 19
239000000243 solution Substances 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CAOHBROWLMCZRP-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanenitrile Chemical compound CC(C)C(C)(N)C#N CAOHBROWLMCZRP-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
ONQSXERGNKDILF-RXMQYKEDSA-N (2r)-2-(2,4-dichlorophenoxy)propanoyl chloride Chemical compound ClC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl ONQSXERGNKDILF-RXMQYKEDSA-N 0.000 description 4
IUOKJNROJISWRO-UHFFFAOYSA-N N-(2-cyano-3-methylbutan-2-yl)-2-(2,4-dichlorophenoxy)propanamide Chemical compound CC(C)C(C)(C#N)NC(=O)C(C)OC1=CC=C(Cl)C=C1Cl IUOKJNROJISWRO-UHFFFAOYSA-N 0.000 description 4
125000005219 aminonitrile group Chemical group 0.000 description 4
239000012071 phase Substances 0.000 description 4
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-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
229940080818 propionamide Drugs 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000012267 brine Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
CAOHBROWLMCZRP-ZCFIWIBFSA-N (2s)-2-amino-2,3-dimethylbutanenitrile Chemical compound CC(C)[C@](C)(N)C#N CAOHBROWLMCZRP-ZCFIWIBFSA-N 0.000 description 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical class NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK1477-2000A 1998-04-20 1999-04-05 Spôsob výroby derivátov N-(1-kyanoalkyl)-2-fenoxypropiónamidu SK14772000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/062,975 US5942640A (en)	1998-04-20	1998-04-20	Process for the manufacture of N-(1-cyanoalkyl)-2-phenoxypropionamide derivatives
PCT/US1999/007443 WO1999054287A1 (en)	1998-04-20	1999-04-05	Improved process for the manufacture of n-(1-cyanoalkyl)-2-phenoxypropionamide derivatives

Publications (1)

Publication Number	Publication Date
SK14772000A3 true SK14772000A3 (sk)	2002-05-09

Family

ID=22046082

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1477-2000A SK14772000A3 (sk)	1998-04-20	1999-04-05	Spôsob výroby derivátov N-(1-kyanoalkyl)-2-fenoxypropiónamidu

Country Status (18)

Country	Link
US (1)	US5942640A (pt)
EP (1)	EP1071659A1 (pt)
JP (1)	JP2002512217A (pt)
KR (1)	KR20010071161A (pt)
CN (1)	CN1298384A (pt)
AR (1)	AR018190A1 (pt)
AU (1)	AU3382499A (pt)
BR (1)	BR9909759A (pt)
CA (1)	CA2328723A1 (pt)
CO (1)	CO4810332A1 (pt)
EA (1)	EA200001020A1 (pt)
HU (1)	HUP0101750A2 (pt)
IL (1)	IL138843A0 (pt)
NZ (1)	NZ507532A (pt)
PL (1)	PL343629A1 (pt)
SK (1)	SK14772000A3 (pt)
WO (1)	WO1999054287A1 (pt)
ZA (1)	ZA200006713B (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001511147A (ja) *	1997-02-04	2001-08-07	ザ・ボード・オブ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・アーカンソー	殺菌・殺カビ性のカルボキサミド類
DE19947613A1 (de) *	1998-10-07	2000-04-13	Sumitomo Chemical Co	Cyanatreinigungsverfahren
EP1155010A1 (en) *	1999-02-20	2001-11-21	AstraZeneca AB	Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s
BR0210912A (pt) *	2001-06-01	2004-08-31	Axys Pharm Inc	Compostos e composições como inibidores de catepsina
CN106366020B (zh) *	2016-08-31	2018-12-11	京博农化科技股份有限公司	一种合成手性稻瘟酰胺的方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA992988A (en) *	1971-06-25	1976-07-13	Don R. Baker	N-(1,1 SUBSTITUTED ACETONITRILO)-.alpha.-(3,5-SUBSTITUTED PHENOXY) ALKYL AMIDES AND THEIR USE AS HERBICIDES
US3932168A (en) *	1971-11-17	1976-01-13	Abbott Laboratories	Substituted aryloxyacetamido nitrile derivatives as carbohydrate deposition agents
US4052432A (en) *	1974-11-18	1977-10-04	Stauffer Chemical Company	N-(1,1 Substituted acetonitrilo)-α-(3,5-substituted phenoxy) alkyl amides
US4087277A (en) *	1976-05-20	1978-05-02	Stauffer Chemical Company	N-(1,1-substituted acetonitrilo)-α-(3,5-substituted phenoxy) alkyl amides and their use as herbicides
AR220917A1 (es) *	1977-10-26	1980-12-15	Stauffer Chemical Co	Compuestos de n-sustituido-2-(4 sustituido-3,5-dimetilfenoxi)butiramida utiles como anublicidas y composicion que los contiene
FR2446812A1 (fr) *	1979-01-16	1980-08-14	Produits Ind Cie Fse	Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides
DE3629441A1 (de) *	1986-08-29	1988-03-03	Celamerck Gmbh & Co Kg	Neue phenoxycarbonsaeurederivate, ihre herstellung und verwendung
JPH059165A (ja) *	1991-02-18	1993-01-19	Mitsubishi Petrochem Co Ltd	置換フエノキシカルボン酸アミド誘導体
JPH0570428A (ja) *	1991-09-13	1993-03-23	Mitsubishi Petrochem Co Ltd	置換フエノキシカルボン酸アミド誘導体およびそれを含有する農業用殺菌剤

1998
- 1998-04-20 US US09/062,975 patent/US5942640A/en not_active Expired - Fee Related
1999
- 1999-04-05 WO PCT/US1999/007443 patent/WO1999054287A1/en not_active Ceased
- 1999-04-05 AU AU33824/99A patent/AU3382499A/en not_active Abandoned
- 1999-04-05 CN CN99805292A patent/CN1298384A/zh active Pending
- 1999-04-05 PL PL99343629A patent/PL343629A1/xx unknown
- 1999-04-05 EA EA200001020A patent/EA200001020A1/ru unknown
- 1999-04-05 JP JP2000544628A patent/JP2002512217A/ja active Pending
- 1999-04-05 BR BR9909759-1A patent/BR9909759A/pt not_active IP Right Cessation
- 1999-04-05 KR KR1020007011599A patent/KR20010071161A/ko not_active Abandoned
- 1999-04-05 IL IL13884399A patent/IL138843A0/xx unknown
- 1999-04-05 HU HU0101750A patent/HUP0101750A2/hu unknown
- 1999-04-05 CA CA002328723A patent/CA2328723A1/en not_active Abandoned
- 1999-04-05 NZ NZ507532A patent/NZ507532A/xx unknown
- 1999-04-05 EP EP99915270A patent/EP1071659A1/en not_active Withdrawn
- 1999-04-05 SK SK1477-2000A patent/SK14772000A3/sk unknown
- 1999-04-15 CO CO99022531A patent/CO4810332A1/es unknown
- 1999-04-19 AR ARP990101806A patent/AR018190A1/es not_active Application Discontinuation
2000
- 2000-11-17 ZA ZA200006713A patent/ZA200006713B/en unknown

Also Published As

Publication number	Publication date
ZA200006713B (en)	2001-11-19
KR20010071161A (ko)	2001-07-28
EP1071659A1 (en)	2001-01-31
CN1298384A (zh)	2001-06-06
US5942640A (en)	1999-08-24
CO4810332A1 (es)	1999-06-30
JP2002512217A (ja)	2002-04-23
EA200001020A1 (ru)	2001-06-25
WO1999054287A1 (en)	1999-10-28
IL138843A0 (en)	2001-10-31
PL343629A1 (en)	2001-08-27
HUP0101750A2 (hu)	2001-10-28
AU3382499A (en)	1999-11-08
BR9909759A (pt)	2000-12-19
CA2328723A1 (en)	1999-10-28
NZ507532A (en)	2002-08-28
AR018190A1 (es)	2001-10-31

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JP2625544B2 (ja)	1997-07-02	Ｎ―（ｒ）―（１―（４―クロロ―フェニル）―エチル）―２，２―ジクロロ―１―エチル―３―メチルシクロプロパンカルボキサミドの立体異性体
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RU2129548C1 (ru)	1999-04-27	Производные амидов аминокислот, способы их получения, сельскохозяйственные или садовые фунгициды и способ уничтожения грибов
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WO2022149098A1 (en)	2022-07-14	Process for preparation of insecticidal anthranilamides
WO2000076960A1 (en)	2000-12-21	Process for the preparation of optically active n-acyl derivatives of methyl n-(2,6-dimethylphenyl)-d-alaninate
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RU2157363C2 (ru)	2000-10-10	Производные валинамида, способ их получения и способы получения промежуточных продуктов
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US4479005A (en)	1984-10-23	Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids
EP0621272B1 (en)	1997-11-19	3,4-Dioxy-1,2,5-thiadiazoles partly useful as fungicides
US5157143A (en)	1992-10-20	Diastereoselective process for the preparation of intermediates useful for the synthesis of peptide derivatives
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KR0142139B1 (ko)	1998-07-01	(+)2-벤조일-3-[(프로피-2(s)-일)아미노]아크릴레이트 유도체의 제조방법
KR0145351B1 (ko)	1998-07-15	2-니트로벤조일-3-실릴옥시아미노아크릴레이트 유도체 및 그 제조방법
CZ20003869A3 (cs)	2001-05-16	Způsob přípravy derivátu N-(l-kyanoalkyl)-2- fenoxypropionamidu
JPH04295469A (ja)	1992-10-20	キノキサリニルオキシフェノキシプロピオン酸の光学活性エステルの製造方法
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