Process for the preparation of (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid and alkyl esters and acid salts thereof

US8324417B2 · kind B2 · utility

Assignee

• Virobay, Inc. · US

Inventors

• Barry Hart · Palo Alto, US
• Jeff Dener · Millbrae, US
• Michael J. Green · Skillman, US
• Michael Charles Henry Standen · Clackmannan, GB
• Oldrich Kocian · Camelford, GB

Key dates

• Filing date: Aug 16, 2010
• Grant date: Dec 4, 2012
• Expiry date: Oct 25, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/02
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a process for the preparation of alkyl esters of (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid, which are intermediates useful in the synthesis of (S)—N-(1-cyanocyclopropyl)-5-cyclopropyl-4,4-difluoro-2-((S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethylamino)pentanamide and related compounds, which are compounds that are cysteine protease inhibitors.