Azetidinones and their production and use

Details Azetidinones and their production and use Azetidinones and their production and use

C - Chemistry, Metallurgy

07

D

260/242.01, 260/

C07D 487/04 (2006.01)

Patent

CA 1102322

Abstract of the Disclosure Improved processes are provided for the production of a variety of azetidinones used in the partial synthesis of .beta.-lactam antibiotics. These processes begin with chlorination of various types of anhydropenicillins to produce sulfur-free dichlorides which react with water or alcohols to produce acids or esters. These esters still contain a chlorine atom which undergoes ready intermolecular nucleophilic displacement by azide, cyanide, acetate or formate ions, or intramolecular displacement to form oxazolines, oxazolidones and oxa-anhydropenicillins. Allylic bromination of these monocyclic and bicyclic azetidinones followed by reaction with azid ion produces an allylic azide group which can be reduced to an allylic amino group. Most of the intermediates so produced are novel. From these compounds there are produced new .beta.-lactam antibiotics such as 1-oxa-benxylpenicillin.

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