Methodology for the Preparation of 2-Argininylbenzothiazole
journal contribution
posted on 2007-12-07, 00:00 authored by Birdella D. Kenney, Michael Breslav, Rosie Chang, Roland Glaser, Bruce D. Harris, Cynthia A. Maryanoff, John Mills, Armin Roessler, Brigitte Segmuller, Frank J. VillaniAn efficient process to produce kilogram quantities of a key
argininylbenzo[d]thiazole intermediate was developed for the
preparation of the tryptase inhibitor RWJ-56423. A variety
of activated arginine esters and benzo[d]thiazole nucleophiles
were evaluated as coupling partners. Our work led to the
selection and optimization of an argininyl imidazolide ester
and benzothiazol-2-yl MgCl nucleophile. This paper focuses
on the preparation, use, and stability of the benzothiazol-2-yl Grignard reagents.
