Process for the enzymatic resolution of N-(alkoxycarbonyl)-4-ketoproline alkyl esters or N-(alkoxycarbonyl)-4-hydroxyproline alkyl esters using Candida antarctica lipase B
US5928933A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jun 26, 1998 |
| Grant date | Jul 27, 1999 |
| Priority date | — |
| Expiry date | Jun 26, 2018 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY10S435/921
- WIPO fieldBiotechnology
- WIPO sectorChemistry
Abstract
The present invention relates to a process for the enzymatic resolution of racemic mixtures of N-(alkoxycarbonyl)-4-keto-D,L-proline alkyl esters, using Candida antarctica lipase fraction B (CALB) as enzyme catalyst to enantioselectively hydrolyze the alkyl ester of one of the two enantiomers present. Separating the unreacted N-(alkoxycarbonyl)-4-keto-D-proline alkyl ester from the N-(alkoxycarbonyl)-4-keto-L-proline, followed by hydrogenation of the keto group of the D-isomer and subsequent hydrolysis of the ester and N-(alkoxy-carbonyl) groups produces cis-4-hydroxy-D-proline in high yield. Diastereomeric mixtures of N-(alkoxycarbonyl)-4-hydroxyproline alkyl esters can also be resolved using CALB to ultimately produce cis-4-hydroxy-D-proline or trans-4-hydroxy-L-proline.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.