Process for the preparation of cephalosporins

Details Process for the preparation of cephalosporins Process for the preparation of cephalosporins

C - Chemistry, Metallurgy

07

D

260/298.2

C07D 513/04 (2006.01) C07D 205/08 (2006.01)

Patent

CA 1060451

ABSTRACT OF THE DISCLOSURE A new process is disclosed for the preparation of com- pounds of structure: Image (I) wherein R is a member selected from the class consisting of hydrogen, alkyl with not more than 12 carbon atoms, cycloalkyl with not more than 12 carbon atoms, alkenyl with not more than 12 carbon atoms, with or without substituents such as a free or a protected hydroxy group, amino, cyano and nitro groups, a thienyl- methyl, furyl-methyl, naphthyl-methyl, cyclohexenyl-methyl, and cyclohexadienyl-methyl, or one of the following groups: Image ; Image ; Image in which X is a member selected from the class consisting of hydrogen, halogen, a free or a protected hydroxy group, alkyl with 1 to 4 carbon atoms, nitro, cyano, and a protected amino group; Y is a protected hydroxy, amino or carboxyl group; n is an integer from 0 to 4; R1 is a member selected from the class consisting of hydroxy, alkoxy having from 1 to 4 carbon atoms, benzyloxy, p-methoxy- benzyloxy, p-nitrobenzyloxy, benzhydryloxy, triphenyl methoxy, phenacyloxy, p-halophenacyloxy, phtalimidomethoxy, an amino group free or substituted by an alkyl having from 1 to 4 carbon atoms, cycloalkyl with 5 to 8 carbon atoms, phenyl, mono-nuclear hetero- cycle, acyloxymethyloxy, acylamidomethyloxy, free or protected hydrazino groups; Abstract continued...... Z is a member selected from the class consisting of hydroxy, -O-Alkyl, -O-CO-Alkyl, O-CO-NH2, -N3, -NH2, -S-Alkyl where the alkyl is an alkyl group with 1 to 4 carbon atoms, -S-Aryl and -S- mononuclear heterocycle containing one or more nitrogen or sulfur atoms; and each R2 is hydrogen or an alkyl group with 1 to 4 carbon atoms and the R2's may be the same or different characterized in that a compound of structure Image (II) where R and R1 have the meanings given above, is reacted in a suitable solvent with a haloamide in the presence of a metal oxide or a haloamide in the presence of a free radical initiator under the influence of light or heat or alternatively with a halogen in the presence of a metal oxide, to give a compound of structure: Image (III) where R and R1 have the meanings given above, Hal is a halogen atom; the intermediate compound (III) in a suitable solvent is then reacted with an appropriate nucleophilic reagent to obtain the compound: Image (IV) Abstract continued...... where R, R1 and Z have the above meanings; the compound (IV) is then subjected to an allylic halo- genation in a suitable solvent by reacting it with a haloamide either under the influence of light alone or by heating it in the presence of a free radical initiator, to give a compound of structure: Image (V) where R, R1 and Hal and Z have the above meanings; the intermediate compound (V) is then reacted with a reducing agent to give finally the desired compound (I).

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