Process for the preparation of luciferin compounds

US4826989A · kind A · utility

Assignee

• Boehringer Mannheim GmbH · DE

Inventors

• Hans-Georg Batz · Tutzing, DE
• Karl Wulff · Weilheim, DE

Key dates

• Filing date: Sep 10, 1987
• Grant date: May 2, 1989
• Expiry date: Sep 10, 2007

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D277/64
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a process for the preparation of compounds of the general formula: ##STR1## in which X is a hydroxyl group and X.sub.1 is a hydrogen atom or a hydroxyl group, and especially of luciferin, by the reaction of D-cysteine with 2-cyanomono- or -dihydroxybenzothiazole obtained from 2-chloromono- or -dimethoxybenzothiazole via a demethylation, wherein the demethylation is accomplished by reaction with iodotrimethylsilane or with a mixture of phenyltrimethylsilane and iodine and hydrolysis under mild conditions of the silyl derivative formed.