title: Methodology for the preparation of 2-argininylbenzothiazole.
abstract: An 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.
authors.affiliation: Johnson & Johnson Pharmaceutical Research and Development, Raritan, New Jersey 08869, USA. birdellakenney@yahoo.com
authors.forename: Birdella D
authors.initials: BD
authors.lastname: Kenney
authors.forename: Michael
authors.initials: M
authors.lastname: Breslav
authors.forename: Rosie
authors.initials: R
authors.lastname: Chang
authors.forename: Roland
authors.initials: R
authors.lastname: Glaser
authors.forename: Bruce D
authors.initials: BD
authors.lastname: Harris
authors.forename: Cynthia A
authors.initials: CA
authors.lastname: Maryanoff
authors.forename: John
authors.initials: J
authors.lastname: Mills
authors.forename: Armin
authors.initials: A
authors.lastname: Roessler
authors.forename: Brigitte
authors.initials: B
authors.lastname: Segmuller
authors.forename: Frank J
authors.initials: FJ
authors.lastname: Villani
mesh_terms: D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D052160:Benzothiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D003460:Crystallization; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D013997:Time Factors
chemical_list: C526563:2-argininylbenzothiazole; D052160:Benzothiazoles; D007093:Imidazoles; D001120:Arginine