Process for 2-chlorosulfinylazetidin-4-ones

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

1977-09-01

1979-06-26

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260239A, 2603322H, 2603472, C07D33324, C07D33338

Patent

active

041592727

ABSTRACT:
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.degree. C. and about 120.degree. 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.-sulfoxide. The latter compounds are useful in the preparation of 3-alkoxy and 3-halo substituted cephalosporin antibiotic compounds.

REFERENCES:
patent: 3843682 (1974-10-01), Kukolja et al.
patent: 4075203 (1978-02-01), Chou
patent: 4081440 (1978-03-01), Kukolja

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