Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl -3- phenyl propanoic acid, application to the synthesis of N-(mercaptoacyl) amino acid derivatives
US6013829A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Nov 26, 1997 |
| Grant date | Jan 11, 2000 |
| Priority date | — |
| Expiry date | Nov 26, 2017 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C327/32
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl-3-phenylpropanoic acid of formula (I): characterized in that it comprises the steps consisting in: PA1 a) preparing the diol (VI) by reduction of a malonic ester (V) in the presence of a hydride; PA1 b) preparing the monoacetates (VII R) or (VII S) respectively; PA1 c) subjecting these monoacetates to an oxidation in order to form the acids (IX S) or (IX R); PA1 d) saponifying the compounds (IX S) or (IX R) in order to form the hydroxy acids (X S) or (X R); PA1 e) thioacylating the hydroxy acids (X S) or (X R) with a mercapto acid R.sub.1 SH (XI), according to a Mitsunobu-type reaction, in order to lead to the desired acids (I R) (I S) respectively and application to the synthesis of N-(mercaptoacyl)amino acid derivatives (II). ##STR1##
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.