JPS5452053A - Separation of threo-isomer and erythro-isomer of 3-amino- hydroxy-4-phenylbutyric acid - Google Patents
Separation of threo-isomer and erythro-isomer of 3-amino- hydroxy-4-phenylbutyric acidInfo
- Publication number
- JPS5452053A JPS5452053A JP11612977A JP11612977A JPS5452053A JP S5452053 A JPS5452053 A JP S5452053A JP 11612977 A JP11612977 A JP 11612977A JP 11612977 A JP11612977 A JP 11612977A JP S5452053 A JPS5452053 A JP S5452053A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- isomer
- amino
- title compound
- solution
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- LDSJMFGYNFIFRK-UHFFFAOYSA-N 3-azaniumyl-2-hydroxy-4-phenylbutanoate Chemical compound OC(=O)C(O)C(N)CC1=CC=CC=C1 LDSJMFGYNFIFRK-UHFFFAOYSA-N 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- LDSJMFGYNFIFRK-BDAKNGLRSA-N (2s,3r)-3-azaniumyl-2-hydroxy-4-phenylbutanoate Chemical compound OC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 LDSJMFGYNFIFRK-BDAKNGLRSA-N 0.000 abstract 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 abstract 1
- VGGGPCQERPFHOB-UHFFFAOYSA-N Bestatin Natural products CC(C)CC(C(O)=O)NC(=O)C(O)C(N)CC1=CC=CC=C1 VGGGPCQERPFHOB-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229950009811 ubenimex Drugs 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To separate the threo-isomer and the erythro-isomer of the title compound useful as an intermediate of a novel physiologically active compound, bestatin, by dissolving a diastereomer mixture of the title compound in an acid, adjusting the pH of the solution to 2.0-3.0, and separating the precipitate.
CONSTITUTION: Diastereomer mixture of the title compound of formula [the steric configuration of amino acid is (2RS, 3R), (2RS, 3S), or (2RS, 3RS)K] is dissolved in an equivalent of acid (mineral acid such as hydrochloric acid, sulfuric acid, etc.), the pH of the solution is adjusted between 2.0 and 3.0 (pref. 2.3 and 2.5) by adding a base (pref. aqueous ammonia), the solution is left to stand at room temperature, and the produced precipitate is separated by filtering. The prcipitate is dissolved in a dilute acid, passed through a strong acidic ion exchange resin, and the adsorbed amino acids are eluted with aqueous ammonia, to obtain an optically pure (2S, 3R)-3- amino-2-hydroxy-4-phenylbutyric acid
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11612977A JPS5452053A (en) | 1977-09-29 | 1977-09-29 | Separation of threo-isomer and erythro-isomer of 3-amino- hydroxy-4-phenylbutyric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11612977A JPS5452053A (en) | 1977-09-29 | 1977-09-29 | Separation of threo-isomer and erythro-isomer of 3-amino- hydroxy-4-phenylbutyric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5452053A true JPS5452053A (en) | 1979-04-24 |
Family
ID=14679424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11612977A Pending JPS5452053A (en) | 1977-09-29 | 1977-09-29 | Separation of threo-isomer and erythro-isomer of 3-amino- hydroxy-4-phenylbutyric acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5452053A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491915A (en) * | 2011-12-02 | 2012-06-13 | 深圳万乐药业有限公司 | Method for preparing ubenimex hydrolysis intermediates |
-
1977
- 1977-09-29 JP JP11612977A patent/JPS5452053A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491915A (en) * | 2011-12-02 | 2012-06-13 | 深圳万乐药业有限公司 | Method for preparing ubenimex hydrolysis intermediates |
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