Preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-P-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines

US6852887B2 · kind B2 · utility

Assignee

• Aerojet Fine Chemicals LLC · US

Inventors

• Aslam A. Malik · Cameron Park, US
• Hasan Palandoken · Woodland, US
• Joy A. Stringer · Rancho Cordova, US
• Roland P. Carlson · Folsom, US
• John Leach · Rancho Cordova, US
• Thomas G. Archibald · Folsom, US
• Robert G. Miotke · Rancho Cordova, US

Key dates

• Filing date: Mar 4, 2003
• Grant date: Feb 8, 2005
• Expiry date: Mar 4, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C303/40
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a new process for the preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride, wherein this compound is prepared directly from the chloromethylalcohol. Importantly, the process of the present invention results in higher yields of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride without sacrificing its purity. The processes of the present invention can be used to prepare not only the 2S,3S-derivative, but also the 2R,3S-, 2S,2R- and the 2R,3R-derivatives.