3-Methylenecephalosporins and process for production thereof

Details 3-Methylenecephalosporins and process for production thereof 3-Methylenecephalosporins and process for production thereof

1971-02-25

1976-01-13

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424246, C07D50118

Patent

active

039323935

ABSTRACT:
3-Methylenecepham-4-carboxylic acids and esters of the Formula I and 3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acids and esters of the Formula II ##SPC1##
where R is hydrogen or an organic acyl group and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl a carboxylic acid protecting group or a pharmaceutically acceptable cation are prepared via the reductive displacement of a 3-substituted methyl cephalosporin of the Formula III ##SPC2##
where R.sub.2 is an organic residue such that --SR.sub.2 constitutes a reductively displaceable moiety, and R and R.sub.1 have the same meanings as defined in Formulae I and II, reductive displacement being accomplished by catalytic hydrogenation or chemical reduction. The 3-methylene cepham compounds are isomerized in dimethylacetamide in the presence of a tertiary alkyl amine to provide 3-methyl-7-acylamido-.DELTA..sup.3 -cephem-4-carboxylic acids and esters.

REFERENCES:
patent: 3647788 (1972-03-01), Clark et al.
patent: 3660395 (1972-05-01), Wright et al.
patent: 3660396 (1972-05-01), Wright

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