Synthesis of nitroalcohol diastereomers

US6462221B1 · kind B1 · utility

Assignee

• Pharm-Eco Laboratories, Inc. · US

Inventors

• Richard L. Gabriel · Swampscott, US
• Adel Moussa · Burlington, US
• Sharon Fitzhenry · Marblehead, US
• Changhua Liu · Carlisle, US
• David A. Swanson · Lexington, US
• Brittany La · Lawrence, US
• Salah A. Zahr · Acton, US
• Yesh P. Sachdeva · Concord, US
• Jurjus Jurayj · Acton, US

Key dates

• Filing date: May 19, 2000
• Grant date: Oct 8, 2002
• Expiry date: May 19, 2020

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a method of preparing a 1-nitro-3-substituted-3-amino-2-propanol diastereomer represented by Structural Formula I: In Structural Formula I, R is an amine protecting group, and R1 is an amino acid side-chain, a protected amino acid side-chain, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted aralkyl or a substituted or unsubstituted heteroaralkyl group. The method involves contacting a 1-nitro-3-substituted-3-amino-2-propanone with a reducing agent to form a mixture of 1-nitro-3-substituted-3-amino-2-propanol diastereomers. The 1-nitro-3-substituted-3-amino-2-propanol diastereomers are then separated by simulated moving bed chromatography to obtain one or more 1-nitro-3-substituted-3-amino-2-propanol diastereomer.