Chemical process for the preparation of intermediates to obtain N-formyl hydroxy-lamine compounds

US7452999B2 · kind B2 · utility

Assignee

• Novartis AG · CH

Inventors

• Mahavir Prashad · East Hanover, US
• Hong-Yong Kim · Whippany, US
• Bin Hu · Mesa, US
• Joel Slade · Flanders, US
• Prasad Koteswara Kapa · Parsippany, US
• Michael John Girgis · Richmond, US

Key dates

• Filing date: Feb 20, 2004
• Grant date: Nov 18, 2008
• Expiry date: Feb 20, 2024

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/07
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Improved processes for preparing intermediates useful for preparing antibacterial N-[1-oxo-2-alkyl-3-(N-hydroxyformamido)-propyl}-(carbonylamino-aryl or -heteroaryl)-azacyclo4-7alkanes or thiazacyclo4-7alkanes, which have one or more of the following features: (1) make use of a particular β-lactam intermediate; (2) which make use of a particular resolving agents, enantiomerically pure substituted propionic acids, especially (R)-2-butyl-3-hydroxy-propionic acid; (3) which avoid the use of hydrogen peroxide; and (4) which facilitate selective debenzylation reducing production of waste by-products.