The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Oct. 23, 2007
Filed:
Oct. 03, 2005
Mukund S. Chorghade, Natick, MA (US);
Rayomand H. Gimi, Chelmsford, MA (US);
Peter D. Mcdonnell, Edmunds, GB;
Paul Wolstenholme-hogg, Haverhill, GB;
Mukund S. Chorghade, Natick, MA (US);
Rayomand H. Gimi, Chelmsford, MA (US);
Peter D. McDonnell, Edmunds, GB;
Paul Wolstenholme-Hogg, Haverhill, GB;
Genzyme Corporation, Cambridge, MA (US);
Abstract
A useful and efficient method of preparing an alkylated thiazoline carboxylic acid, or a derivative thereof, comprises coupling a substituted aryl nitrile such as, for example, 2,4-dimethoxybenzonitrile or 4-methoxybenzonitrile, with a cysteine ester to form a substituted thiazoline carboxylic acid ester; optionally hydrolyzing the substituted thiazoline carboxylic acid ester to form a substituted thiazoline carboxylic acid; optionally, protecting the carboxyl group; alkylating the thiazoline ring at the 4-carbon position, as indicated in Structural Formula (I), with a compound of the formula R-L, wherein Ris as defined above and L is a leaving group, in the presence of a phase transfer catalyst; and, optionally, deprotecting the carboxyl group. In one embodiment of the present invention, a cinchona-alkaloid derived phase transfer catalyst is used to alkylate a protected substituted thiazoline carboxylic acid.