Process for 2-chlorosulfinylazetidin-4-ones

Details Process for 2-chlorosulfinylazetidin-4-ones Process for 2-chlorosulfinylazetidin-4-ones

C - Chemistry, Metallurgy

07

D

260/336, 260/328

C07D 205/08 (2006.01) C07D 403/12 (2006.01)

Patent

CA 1111049

Abstract of the Disclosure Penicillin sulfoxide esters having the sulfoxide group in the .alpha.-configuration are reacted with an N-chloro halogenating agent at a temperature between about 70°C. and about 120°C. in the presence of an alkylene oxide and preferably also calcium oxide to produce 2-chlorosulfinyl- azetidin-4-one intermediates. The chlorosulfinyl intermediates are then treated with a Friedel-Crafts catalyst, for example, stannic chloride to provide a 3-exomethylenecepham .beta.-sul- foxide. The latter compounds are useful in the preparation of 3-alkoxy and 3-halo substituted cephalosporin antibiotic compounds.

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