IE37316B1 - Processes for the production of optically active esters of alpha-amine acids - Google Patents
Processes for the production of optically active esters of alpha-amine acidsInfo
- Publication number
- IE37316B1 IE37316B1 IE282/73A IE28273A IE37316B1 IE 37316 B1 IE37316 B1 IE 37316B1 IE 282/73 A IE282/73 A IE 282/73A IE 28273 A IE28273 A IE 28273A IE 37316 B1 IE37316 B1 IE 37316B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- prepared
- acid
- hydroxyphenylglycinate
- optically active
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title abstract 6
- 239000002253 acid Substances 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 235000008206 alpha-amino acids Nutrition 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- -1 α-amino acid esters Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- CSJCEQXZVMIHRX-UHFFFAOYSA-N 2,3-dibenzyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1CC(O)(C(O)=O)C(O)(C(=O)O)CC1=CC=CC=C1 CSJCEQXZVMIHRX-UHFFFAOYSA-N 0.000 abstract 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- CVWJDUUVFSVART-UHFFFAOYSA-N ethyl 2-amino-2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)C(N)C1=CC=C(O)C=C1 CVWJDUUVFSVART-UHFFFAOYSA-N 0.000 abstract 1
- MLSGRWDEDYJNER-UHFFFAOYSA-N ethyl 2-anilinoacetate Chemical compound CCOC(=O)CNC1=CC=CC=C1 MLSGRWDEDYJNER-UHFFFAOYSA-N 0.000 abstract 1
- 150000002373 hemiacetals Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical class CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- SZBDOFWNZVHVGR-UHFFFAOYSA-N methyl 2-amino-2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)C(N)C1=CC=C(O)C=C1 SZBDOFWNZVHVGR-UHFFFAOYSA-N 0.000 abstract 1
- BXPNTXBBAVYAMD-UHFFFAOYSA-N phenyl 2-aminoacetate Chemical class NCC(=O)OC1=CC=CC=C1 BXPNTXBBAVYAMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000005331 phenylglycines Chemical class 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- 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
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- 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
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB890272A GB1423822A (en) | 1972-02-25 | 1972-02-25 | Processes for the production of optically active esters of a-amino acids |
| GB5943172 | 1972-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37316L IE37316L (en) | 1973-08-25 |
| IE37316B1 true IE37316B1 (en) | 1977-06-22 |
Family
ID=26242495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE282/73A IE37316B1 (en) | 1972-02-25 | 1973-02-23 | Processes for the production of optically active esters of alpha-amine acids |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3976680A (instruction) |
| JP (1) | JPS5640709B2 (instruction) |
| AT (1) | AT343630B (instruction) |
| BE (1) | BE795874A (instruction) |
| CA (1) | CA1010055A (instruction) |
| CH (1) | CH595301A5 (instruction) |
| DE (1) | DE2309180A1 (instruction) |
| FR (1) | FR2173232B1 (instruction) |
| GB (1) | GB1423822A (instruction) |
| IE (1) | IE37316B1 (instruction) |
| IT (1) | IT994722B (instruction) |
| NL (1) | NL7302544A (instruction) |
| SE (1) | SE419080B (instruction) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2384747A1 (fr) * | 1975-10-06 | 1978-10-20 | Fujisawa Pharmaceutical Co | Imines et procede pour leur preparation |
| US4185116A (en) * | 1976-09-28 | 1980-01-22 | Pfizer Inc. | L- and DL- Phenylglycines to treat diseases or conditions attributable to reduced carbohydrate metabolism |
| US4186210A (en) * | 1976-09-28 | 1980-01-29 | Pfizer Inc. | Method of treatment with glycinamides |
| US4179521A (en) * | 1976-09-28 | 1979-12-18 | Pfizer Inc. | L- and DL-Phenylglycines to treat diseases or conditions attributable to reduced carbohydrate metabolism |
| US4179520A (en) * | 1976-09-28 | 1979-12-18 | Pfizer Inc. | L- and DL-Phenylglycines to treat a disease or condition attributable to reduced blood flow |
| GB1547206A (en) * | 1976-09-28 | 1979-06-06 | Pfizer Ltd | Pharmaceutical compositions |
| US4217284A (en) * | 1976-10-05 | 1980-08-12 | Kowa Company Ltd. | Process for preparation of optically pure lactones from monoesters of cis-cyclopentenediol |
| GB1561314A (en) * | 1976-10-05 | 1980-02-20 | Kowa Co | Monoesters of cis - cyclopentenedio process for preparation thereof and process for preparation of lactones from the monoesters |
| NL187110C (nl) * | 1976-11-10 | 1991-06-03 | Stamicarbon | Werkwijze voor het scheiden van een mengsel van een optisch aktief fenylglycine-amide en een optisch aktief fenylglycine. |
| US4072698A (en) * | 1976-12-02 | 1978-02-07 | The Upjohn Company | Resolution of aminonitriles |
| JPS581105B2 (ja) * | 1977-03-24 | 1983-01-10 | 日本化薬株式会社 | 光学活性アミノ酸−マンデル酸複合体及びその製造法 |
| JPS5945669B2 (ja) * | 1977-06-30 | 1984-11-07 | 住友化学工業株式会社 | 光学活性リジンエステルのラセミ化法 |
| DE2862056D1 (en) * | 1977-08-30 | 1982-11-11 | Riedel De Haen Ag | Process for preparing optically active unsubstituted or substituted 2-amino-2-phenyl-acetic acids |
| DE2749203C2 (de) * | 1977-11-03 | 1981-12-17 | Riedel-De Haen Ag, 3016 Seelze | Verfahren zur Racematspaltung von DL-alpha-Aminocarbonsäuren und diastereomere Salze |
| JPS54109912A (en) * | 1978-02-14 | 1979-08-29 | Ajinomoto Co Inc | Racemization of optically active amino acid ester |
| FR2430413A1 (fr) * | 1978-07-07 | 1980-02-01 | Anvar | Procede de preparation d'alpha-aminoacides optiquement actifs, et leurs derives |
| US4401820A (en) * | 1981-01-23 | 1983-08-30 | Tanabe Seiyaku Co., Ltd. | Process for racemizing optically active α-amino acids or a salt thereof |
| JPS5810544A (ja) * | 1981-07-09 | 1983-01-21 | Tanabe Seiyaku Co Ltd | 光学活性ｐ−ヒドロキシフエニルグリシン塩の製法 |
| DE3209232A1 (de) * | 1982-03-13 | 1983-09-22 | Degussa Ag, 6000 Frankfurt | Verfahren zur racemisierung von optisch aktivem s-(carboxymethyl)-cystein |
| US4542234A (en) * | 1983-10-06 | 1985-09-17 | Usv Pharmaceutical Corp. | Process for the separation of (S,S) diastereoisomers |
| NL8501093A (nl) * | 1985-04-12 | 1986-11-03 | Stamicarbon | Werkwijze voor het racemiseren van een optisch aktief n- benzylideenaminozuuramide. |
| DE3844992B4 (de) * | 1987-03-04 | 2006-06-14 | Novartis Ag | Hydrogentartrat eines Phenylcarbamats |
| JPH07116115B2 (ja) * | 1987-07-24 | 1995-12-13 | 田辺製薬株式会社 | 光学活性アスパラギン酸β−メチルエステル塩の製法 |
| JPH01149775A (ja) * | 1987-12-07 | 1989-06-12 | Kawaken Fine Chem Co Ltd | 光学活性２−メチルピペラジンの製造方法 |
| US5420151A (en) * | 1989-12-22 | 1995-05-30 | Aktiebolaget Astra | Chroman derivatives |
| NL9000386A (nl) * | 1990-02-16 | 1991-09-16 | Stamicarbon | Werkwijze voor de bereiding van optisch aktief aminozuuramide. |
| US5631031A (en) * | 1994-06-13 | 1997-05-20 | Meade; Thomas L. | Water-insoluble amino acid salt |
| DE4443892A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | 4-(Chinolin-2-yl-methoxy)-phenyl-essigsäurederivate |
| SE9601600D0 (sv) * | 1996-04-26 | 1996-04-26 | Astra Ab | Improved process |
| FR2760452B1 (fr) * | 1997-03-05 | 1999-05-28 | Sanofi Sa | Procede d'obtention d'enantiomeres d'acides alpha-amines et sels diastereoisomeriques intermediaires |
| DE19955283A1 (de) * | 1999-11-17 | 2001-05-23 | Aventis Res & Tech Gmbh & Co | Verfahren zur enantioselektiven Gewinnung von Aminosäuren und Aminosäurederivaten unter Verwendung von Racemisierungskatalysatoren |
| US6812363B2 (en) * | 2002-10-15 | 2004-11-02 | Usv Limited | Racemization of optically active 2-substituted phenyl glycine esters |
| CA2505797A1 (en) * | 2002-11-12 | 2004-05-27 | Pfizer Products Inc. | Process for converting a cis-trans mixture of substituted benzylidene amines into the pure cis isomer |
| WO2005103005A1 (ja) * | 2004-04-26 | 2005-11-03 | Astellas Pharma Inc. | β－ピリジルアラニンの光学活性体の選択的製造方法 |
| WO2006003671A1 (en) * | 2004-07-02 | 2006-01-12 | Srinivasa Reddy Battula | A process for resolution of methylamino(2-chlorophenyl)acetate |
| US9493400B2 (en) * | 2012-03-30 | 2016-11-15 | Merck Sharp & Dohme Corp. | Process for preparing fluoroleucine alkyl esters |
| CN110467539B (zh) * | 2019-08-30 | 2023-01-06 | 浙江普洛家园药业有限公司 | 一种2，6-二甲基酪氨酸酯的拆分方法及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1389217A (en) * | 1971-06-02 | 1975-04-03 | Glaxo Lab Ltd | Phenylglycine derivatives |
-
0
- BE BE795874D patent/BE795874A/xx not_active IP Right Cessation
-
1972
- 1972-02-25 GB GB890272A patent/GB1423822A/en not_active Expired
-
1973
- 1973-02-23 US US05/335,304 patent/US3976680A/en not_active Expired - Lifetime
- 1973-02-23 AT AT162373A patent/AT343630B/de not_active IP Right Cessation
- 1973-02-23 CH CH265773A patent/CH595301A5/xx not_active IP Right Cessation
- 1973-02-23 IE IE282/73A patent/IE37316B1/xx unknown
- 1973-02-23 IT IT48414/73A patent/IT994722B/it active
- 1973-02-23 CA CA164,460A patent/CA1010055A/en not_active Expired
- 1973-02-23 JP JP2199273A patent/JPS5640709B2/ja not_active Expired
- 1973-02-23 FR FR7306451A patent/FR2173232B1/fr not_active Expired
- 1973-02-23 DE DE19732309180 patent/DE2309180A1/de not_active Ceased
- 1973-02-23 NL NL7302544A patent/NL7302544A/xx not_active Application Discontinuation
- 1973-02-23 SE SE7302593A patent/SE419080B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT994722B (it) | 1975-10-20 |
| JPS5640709B2 (instruction) | 1981-09-22 |
| SE419080B (sv) | 1981-07-13 |
| NL7302544A (instruction) | 1973-08-28 |
| JPS4897801A (instruction) | 1973-12-13 |
| GB1423822A (en) | 1976-02-04 |
| FR2173232A1 (instruction) | 1973-10-05 |
| DE2309180A1 (de) | 1973-08-30 |
| CA1010055A (en) | 1977-05-10 |
| ATA162373A (de) | 1977-10-15 |
| FR2173232B1 (instruction) | 1977-12-30 |
| BE795874A (fr) | 1973-08-23 |
| IE37316L (en) | 1973-08-25 |
| AT343630B (de) | 1978-06-12 |
| CH595301A5 (instruction) | 1978-02-15 |
| AU5255473A (en) | 1974-08-29 |
| US3976680A (en) | 1976-08-24 |
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