AR006639A1 - Procedimiento mejorado para la produccion de acido azetidina-2-carboxilico enantiomericamente puro - Google Patents
Procedimiento mejorado para la produccion de acido azetidina-2-carboxilico enantiomericamente puroInfo
- Publication number
- AR006639A1 AR006639A1 ARP970101487A ARP970101487A AR006639A1 AR 006639 A1 AR006639 A1 AR 006639A1 AR P970101487 A ARP970101487 A AR P970101487A AR P970101487 A ARP970101487 A AR P970101487A AR 006639 A1 AR006639 A1 AR 006639A1
- Authority
- AR
- Argentina
- Prior art keywords
- acid
- azetidine
- carboxylic acid
- enantiomerically pure
- production
- Prior art date
Links
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 title abstract 8
- IADUEWIQBXOCDZ-VKHMYHEASA-N Azetidine-2-carboxylic acid Natural products OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 6
- 150000007524 organic acids Chemical class 0.000 abstract 3
- 238000010956 selective crystallization Methods 0.000 abstract 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 2
- 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 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 239000012456 homogeneous solution Substances 0.000 abstract 2
- 235000002906 tartaric acid Nutrition 0.000 abstract 2
- 239000011975 tartaric acid Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003892 tartrate salts Chemical class 0.000 abstract 1
Classifications
-
- 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
- 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
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para la producción de ácido azetidin-2-carboxílico enantioméricamente puro que comprende la cristalización selectiva de una sal dedicho ácido enantioméricamente pura a partir de una solución homogénea de ácidoazetidin-2-carb oxílico, ácido tartárico ópticamente activo, un ácido orgánico yun aldehído seguido por la liberación del aminoácido libre. Asimismo se refiere a un procedimiento para la conversión del enantiómero del mencionado ácido dela forma D-a la forma L- y v iceversa por cristalización selectiva de una sal de D- tartrato de L- ácido ( o bien de L- tartrato de D-ácido)diastereoméricamente pura a partir de una solución homogénea de D-ácido respectivamente de L-ácido)azetidin-2-carboxílico, ácido tartárico, un ácidoorgánico y un alcohol seguido de liberación del aminoácido libre. Dicho ácido orgánico puede usarse como solvente; y dicho aldehído puede ser butírico ocaproico. La cristalización selectiva se logramediante una temperatura en e l rango comprendido entre -10 y 30*C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9601600A SE9601600D0 (sv) | 1996-04-26 | 1996-04-26 | Improved process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR006639A1 true AR006639A1 (es) | 1999-09-08 |
Family
ID=20402360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP970101487A AR006639A1 (es) | 1996-04-26 | 1997-04-14 | Procedimiento mejorado para la produccion de acido azetidina-2-carboxilico enantiomericamente puro |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6143903A (es) |
| EP (1) | EP0906255B1 (es) |
| JP (2) | JP2000509068A (es) |
| KR (1) | KR100447072B1 (es) |
| CN (1) | CN1071292C (es) |
| AR (1) | AR006639A1 (es) |
| AT (1) | ATE200889T1 (es) |
| AU (1) | AU713519B2 (es) |
| BR (1) | BR9708872A (es) |
| CA (1) | CA2253711C (es) |
| CZ (1) | CZ339998A3 (es) |
| DE (1) | DE69704708T2 (es) |
| DK (1) | DK0906255T3 (es) |
| EE (1) | EE9800365A (es) |
| EG (1) | EG20975A (es) |
| ES (1) | ES2158557T3 (es) |
| GR (1) | GR3036303T3 (es) |
| HU (1) | HUP9901665A3 (es) |
| ID (1) | ID16840A (es) |
| IL (1) | IL126717A (es) |
| IN (1) | IN186439B (es) |
| IS (1) | IS4860A (es) |
| MY (1) | MY132450A (es) |
| NO (1) | NO310404B1 (es) |
| NZ (1) | NZ332155A (es) |
| PL (1) | PL329685A1 (es) |
| PT (1) | PT906255E (es) |
| SE (1) | SE9601600D0 (es) |
| SK (1) | SK140898A3 (es) |
| TR (1) | TR199802146T2 (es) |
| WO (1) | WO1997041084A1 (es) |
| ZA (1) | ZA973156B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69813053T2 (de) * | 1997-01-24 | 2004-02-19 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von optisch aktiven Azetidin-2-Carbonsäurederivaten |
| SE9802939D0 (sv) | 1998-09-01 | 1998-09-01 | Astra Ab | New process |
| SE9901712D0 (sv) | 1999-05-11 | 1999-05-11 | Astra Ab | New process |
| 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 |
| CN102143928A (zh) * | 2008-09-05 | 2011-08-03 | 马克斯普朗克科学促进协会 | 利用两个连续的结晶步骤对化合物形成的手性体系进行对映体拆分的方法 |
| JP2013241338A (ja) * | 2010-09-09 | 2013-12-05 | Mitsubishi Gas Chemical Co Inc | 光学活性２−アミノ酪酸の製造方法 |
| JP2013241339A (ja) * | 2010-09-09 | 2013-12-05 | Mitsubishi Gas Chemical Co Inc | 光学活性アミノ酸の製造方法 |
| CN103204783B (zh) * | 2013-04-18 | 2015-09-02 | 张家港市华昌药业有限公司 | 一种d-赖氨酸盐酸盐的制备方法 |
| WO2016021711A1 (ja) * | 2014-08-07 | 2016-02-11 | 株式会社エーピーアイ コーポレーション | アミノ酸誘導体の製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795874A (fr) * | 1972-02-25 | 1973-08-23 | Glaxo Lab Ltd | Procede de preparation d'esters optiquement actifs d'alpha-amino-acides |
| JPS5139219B2 (es) * | 1972-06-08 | 1976-10-26 | ||
| US4072698A (en) * | 1976-12-02 | 1978-02-07 | The Upjohn Company | Resolution of aminonitriles |
| JPS56104866A (en) * | 1980-01-24 | 1981-08-20 | Mitsubishi Chem Ind Ltd | Production of (2r,4r)-4-alkyl-2-piperidinecarboxylic acid or its l-tartarate salt |
| DE3303112A1 (de) * | 1983-01-31 | 1984-08-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur racemattrennung optisch aktiver bicyclischer imino-(alpha)-carbonsaeuren |
| US4923983A (en) * | 1989-07-31 | 1990-05-08 | Eli Lilly And Company | Method of resolving cis 3-amino-4-[2-(2-furyl)eth-1-yl]-1-methoxycarbonylmethyl-azetidin-2-one |
| EP0499376A1 (en) * | 1991-01-31 | 1992-08-19 | Hoechst Celanese Corporation | Precipitation-induced asymmetric transformation of chiral alpha-amino acids and salts thereof |
| GB9420246D0 (en) * | 1994-10-07 | 1994-11-23 | Chiroscience Ltd | Asymmetric crystallisation |
| IN187238B (es) * | 1995-06-30 | 2002-03-09 | Astra Ab | |
| DE69722538T2 (de) * | 1996-09-06 | 2004-04-29 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von optisch aktiver Azetidin-2-Carbonsäure |
-
1996
- 1996-04-26 SE SE9601600A patent/SE9601600D0/xx unknown
-
1997
- 1997-04-14 AR ARP970101487A patent/AR006639A1/es unknown
- 1997-04-14 ZA ZA9703156A patent/ZA973156B/xx unknown
- 1997-04-22 CA CA002253711A patent/CA2253711C/en not_active Expired - Fee Related
- 1997-04-22 HU HU9901665A patent/HUP9901665A3/hu unknown
- 1997-04-22 BR BR9708872A patent/BR9708872A/pt not_active Application Discontinuation
- 1997-04-22 SK SK1408-98A patent/SK140898A3/sk unknown
- 1997-04-22 IL IL12671797A patent/IL126717A/en not_active IP Right Cessation
- 1997-04-22 KR KR10-1998-0708557A patent/KR100447072B1/ko not_active Expired - Fee Related
- 1997-04-22 DK DK97921046T patent/DK0906255T3/da active
- 1997-04-22 CZ CZ983399A patent/CZ339998A3/cs unknown
- 1997-04-22 EE EE9800365A patent/EE9800365A/xx unknown
- 1997-04-22 AT AT97921046T patent/ATE200889T1/de not_active IP Right Cessation
- 1997-04-22 DE DE69704708T patent/DE69704708T2/de not_active Expired - Lifetime
- 1997-04-22 CN CN97194111A patent/CN1071292C/zh not_active Expired - Fee Related
- 1997-04-22 JP JP9538797A patent/JP2000509068A/ja active Pending
- 1997-04-22 WO PCT/SE1997/000675 patent/WO1997041084A1/en not_active Ceased
- 1997-04-22 TR TR1998/02146T patent/TR199802146T2/xx unknown
- 1997-04-22 US US08/913,016 patent/US6143903A/en not_active Expired - Fee Related
- 1997-04-22 PL PL97329685A patent/PL329685A1/xx unknown
- 1997-04-22 NZ NZ332155A patent/NZ332155A/xx not_active IP Right Cessation
- 1997-04-22 ES ES97921046T patent/ES2158557T3/es not_active Expired - Lifetime
- 1997-04-22 PT PT97921046T patent/PT906255E/pt unknown
- 1997-04-22 AU AU27194/97A patent/AU713519B2/en not_active Ceased
- 1997-04-22 EP EP97921046A patent/EP0906255B1/en not_active Expired - Lifetime
- 1997-04-23 MY MYPI97001747A patent/MY132450A/en unknown
- 1997-04-23 EG EG32897A patent/EG20975A/xx active
- 1997-04-24 IN IN1060DE1997 patent/IN186439B/en unknown
- 1997-04-25 ID IDP971396A patent/ID16840A/id unknown
-
1998
- 1998-10-06 IS IS4860A patent/IS4860A/is unknown
- 1998-10-07 NO NO19984681A patent/NO310404B1/no not_active IP Right Cessation
-
2001
- 2001-07-31 GR GR20010401153T patent/GR3036303T3/el unknown
-
2008
- 2008-11-13 JP JP2008290436A patent/JP2009120611A/ja active Pending
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