NL9301303A - Werkwijze voor de bereiding van L-fenylalanine methylester en werkwijze voor het daaruit bereiden van alfa-L-aspartyl-L-fenylalanine methylester. - Google Patents
Werkwijze voor de bereiding van L-fenylalanine methylester en werkwijze voor het daaruit bereiden van alfa-L-aspartyl-L-fenylalanine methylester. Download PDFInfo
- Publication number
- NL9301303A NL9301303A NL9301303A NL9301303A NL9301303A NL 9301303 A NL9301303 A NL 9301303A NL 9301303 A NL9301303 A NL 9301303A NL 9301303 A NL9301303 A NL 9301303A NL 9301303 A NL9301303 A NL 9301303A
- Authority
- NL
- Netherlands
- Prior art keywords
- methyl ester
- aspartyl
- phenylalanine methyl
- phenylalanine
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 41
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 title claims description 19
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- 239000013078 crystal Substances 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 229960005190 phenylalanine Drugs 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000006344 deformylation reaction Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- OSEHTEQTVJQGDE-RYUDHWBXSA-N (3s)-3-formamido-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 OSEHTEQTVJQGDE-RYUDHWBXSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 230000006198 deformylation Effects 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- DFTMVZIUYVECNW-VKHMYHEASA-N n-[(3s)-2,5-dioxooxolan-3-yl]formamide Chemical compound O=CN[C@H]1CC(=O)OC1=O DFTMVZIUYVECNW-VKHMYHEASA-N 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- WYYUBJAMROQJSF-QWRGUYRKSA-N (3s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-formamido-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 WYYUBJAMROQJSF-QWRGUYRKSA-N 0.000 claims 1
- JZSZFHRYZNUIMY-UHFFFAOYSA-N methane tetrahydrochloride Chemical compound C.Cl.Cl.Cl.Cl JZSZFHRYZNUIMY-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- 230000035484 reaction time Effects 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229960005261 aspartic acid Drugs 0.000 description 2
- -1 for example Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 108010011485 Aspartame Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93596192A | 1992-08-27 | 1992-08-27 | |
| US93596192 | 1992-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL9301303A true NL9301303A (nl) | 1994-03-16 |
Family
ID=25467976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9301303A NL9301303A (nl) | 1992-08-27 | 1993-07-23 | Werkwijze voor de bereiding van L-fenylalanine methylester en werkwijze voor het daaruit bereiden van alfa-L-aspartyl-L-fenylalanine methylester. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5334746A (it) |
| KR (1) | KR970009594B1 (it) |
| CH (1) | CH687825A5 (it) |
| DE (1) | DE4328967A1 (it) |
| FR (1) | FR2695128B1 (it) |
| GB (1) | GB2270311B (it) |
| IT (1) | IT1270852B (it) |
| NL (1) | NL9301303A (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010096940A (ko) * | 2000-04-19 | 2001-11-08 | 고두모 | 알파-엘-아스파틸-엘-페닐알라닌 메틸에스테르 염산염의제조방법 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3786039A (en) * | 1969-04-30 | 1974-01-15 | Ajinomoto Kk | Method of producing alpha-l-aspartyl-l-phenylalanine lower alkyl esters |
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| US4680403A (en) * | 1985-01-17 | 1987-07-14 | Ajinomoto Co., Inc. | Process for producing N-protected-α-L-aspartyl-L-phenylalanine methyl ester |
| US4684745A (en) * | 1982-04-22 | 1987-08-04 | Ajinomoto Company Incorporated | Process for producing α-L-aspartyl-L-phenylalanine methyl ester for its hydrochloride |
| KR910007940B1 (ko) * | 1989-04-14 | 1991-10-04 | 주식회사 미원 | L-페닐알라닌 메틸에스테르 염산염의 정석법 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492131A (en) * | 1966-04-18 | 1970-01-27 | Searle & Co | Peptide sweetening agents |
| JPS5223001A (en) * | 1975-08-14 | 1977-02-21 | Ajinomoto Co Inc | Process for elimination of formyl group |
| DE3600731A1 (de) * | 1986-01-13 | 1987-07-16 | Green Cross Korea | Verfahren zur herstellung von (alpha)-l-aspartyl-l-phenylalaninmethylester |
| JPH0657719B2 (ja) * | 1986-06-03 | 1994-08-03 | 味の素株式会社 | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの回収方法 |
-
1993
- 1993-05-14 IT ITTO930336A patent/IT1270852B/it active IP Right Grant
- 1993-05-28 FR FR9306439A patent/FR2695128B1/fr not_active Expired - Fee Related
- 1993-07-23 NL NL9301303A patent/NL9301303A/nl active Search and Examination
- 1993-08-13 CH CH02407/93A patent/CH687825A5/de not_active IP Right Cessation
- 1993-08-17 GB GB9317124A patent/GB2270311B/en not_active Expired - Fee Related
- 1993-08-26 KR KR93016693A patent/KR970009594B1/ko not_active Expired - Fee Related
- 1993-08-27 DE DE4328967A patent/DE4328967A1/de not_active Withdrawn
- 1993-12-06 US US08/161,437 patent/US5334746A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3786039A (en) * | 1969-04-30 | 1974-01-15 | Ajinomoto Kk | Method of producing alpha-l-aspartyl-l-phenylalanine lower alkyl esters |
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| US4684745A (en) * | 1982-04-22 | 1987-08-04 | Ajinomoto Company Incorporated | Process for producing α-L-aspartyl-L-phenylalanine methyl ester for its hydrochloride |
| US4680403A (en) * | 1985-01-17 | 1987-07-14 | Ajinomoto Co., Inc. | Process for producing N-protected-α-L-aspartyl-L-phenylalanine methyl ester |
| KR910007940B1 (ko) * | 1989-04-14 | 1991-10-04 | 주식회사 미원 | L-페닐알라닌 메틸에스테르 염산염의 정석법 |
Non-Patent Citations (1)
| Title |
|---|
| DATABASE WPI Week 9248, Derwent World Patents Index; AN 92-395930 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2695128B1 (fr) | 1995-07-07 |
| FR2695128A1 (fr) | 1994-03-04 |
| ITTO930336A0 (it) | 1993-05-14 |
| GB2270311A (en) | 1994-03-09 |
| DE4328967A1 (de) | 1994-03-03 |
| GB2270311B (en) | 1996-10-02 |
| US5334746A (en) | 1994-08-02 |
| CH687825A5 (de) | 1997-02-28 |
| KR940003905A (ko) | 1994-03-14 |
| KR970009594B1 (en) | 1997-06-14 |
| ITTO930336A1 (it) | 1994-11-14 |
| IT1270852B (it) | 1997-05-13 |
| GB9317124D0 (en) | 1993-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1A | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable |