Process for the manufacture of 4-thioazetidinone compounds

Details Process for the manufacture of 4-thioazetidinone compounds Process for the manufacture of 4-thioazetidinone compounds

1984-04-20

1986-05-06

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602454, 2603303, 2603309, 544 54, 544 585, 544111, 544335, 544359, C07D20508, C07D40106, C07D40306, C07D40112

Patent

active

045870489

ABSTRACT:
The present invention relates to a novel process for the manufacture of 4-thioazetidinone compounds of the formula ##STR1## in which R.sub.1.sup.a represents an amino-protecting group and R.sub.1.sup.b represents hydrogen or an acyl radical Ac, or in which R.sub.1.sup.a and R.sub.1.sup.b together represent a bivalent acyl radical, R.sub.2.sup.A represents an etherified hydroxy group, R.sub.3 represents methyl, hydroxy, etherified or esterified hydroxy, cyano, tertiary amino or nitro, X represents hydrogen or halogen, and Y represents a group --SR.sub.4 or --SO.sub.2 --R.sub.5 in which R.sub.4 represents an optionally substituted heteroaryl radical or the acyl radical of an organic carboxylic or thiocarboxylic acid and R.sub.5 represents an optionally substituted hydrocarbon radical, or, when R.sub.3 represents hydroxy or methyl, tautomers thereof. Compounds of the formula I are manufactured by reacting compounds of the formula III with a nitrosating agent and a compound of the formula IV. Antibiotically active 3-cephem acid derivatives can be manufactured from the compounds of the formula I. The invention relates also to the novel intermediates of the formula III.

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