Process for the preparation of 3-chloro-cefem compounds

Details Process for the preparation of 3-chloro-cefem compounds Process for the preparation of 3-chloro-cefem compounds

1992-03-11

1993-07-20

Page, Thurman K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540215, C07D50104

Patent

active

052295095

ABSTRACT:
The process comprises a series of stages essentially comprising the protection of the functional groups of the side chain of Ampicillin, esterification of the acid group, oxidation to sulphoxide, expansion of the thiazole ring to a thiazine ring, ozonolysis of the exomethylene cefam derivative obtained, substitution of the hydroxyl group by chlorine and de-protection of the functional groups, in which the order of some stages can be varied without affecting the final result.

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patent: 3691188 (1972-09-01), Spry
patent: 3714146 (1973-01-01), Gottstein et al.
patent: 3925372 (1975-12-01), Chauvette
patent: 4113940 (1978-09-01), Kamiya et al.
patent: 4473567 (1984-09-01), Ko'oka et al.
patent: 4513134 (1985-04-01), Kim et al.
Advanced Organic Chemistry by Jerry March pp. 382-384, 2nd edition McGraw Hill Book Company (1977).
Pharmazeutische Wirkstoffe, von A. Kleeman, Georg Thieme Verlag, Stuttgart and New York, 1982.
Biochemicals, Organic Compounds For Research and Diagnostic Reagents, Sigma Chemical Company, pp. 112 and 230 (1991).
S. Kukolja, J. Chem. Soc. 28: 181 (1977).

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