Nuclear analogs of β-lactam antibiotics. VI. Synthesis ofN-2-isocephems
摘要：
The syntheses ofN-methyl andN-carboethoxy-7-β-phenoxyacetamido-Δ3-N-2-isocephem-4-carboxylic acids17aand17bare reported. Treatment of aldehyde3cwith methylamine followed by reduction of the Schiff base gave4dwhich was converted to its trifluoroacetamide5c. Acid catalyzed elimination of a mole of ethanol from5c, gave8bwhich was converted to the enol10bvia the vinylogous pyrrolidino amide9b. Reductive removal of the trifluoroacetamide function led to spontaneous ring closure to give11b. Alternatively treatment of bis-mesylate12bwith ammonia or methylamine gave13aand13b, respectively. Treatment of13bwith sodium hydride in DMSO gave11b. Attempted acylation of13agave14. Reduction of the azido functions in11band14followed by coupling of the amines to phenoxyacetic acid and reductive removal of the benzyl esters gave17aand17b, respectively. The structural assignments are discussed.
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DOI：
10.1139/v77-377
年份：
1977
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