Acetic Acid → HCID 70503795, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 9.5 g (50 mmols) of titanium(IV) chloride and 5.67 g (150 mmols) of sodium borohydride in 150 ml of dimethoxy ethane is slowly added, at -20° C., a suspension of 10.86 g (20 mmols) of 7β-[2-(2-thienyl)-acetylamino]-3-pyrrolidino-3-cephem-4-carboxylic acid p-nitrobenzyl ester 1-oxide in 150 ml of ethylene glycol dimethyl ether, so that the temperature does not rise above -15° C. When the addition is complete, the reaction mixture is warmed to 0° C. and then a mixture of 50 ml of glacial acetic acid and 50 ml of ethylene glycol dimethyl ether is added dropwise. The reaction mixture is then stirred for 36 hours at room temperature. While cooling with ice, 200 ml of ice-water are cautiously added dropwise to the blue reaction solution. After extraction with three 150 ml portions of methylene chloride, the organic phase is dried over sodium sulfate and the solvent is removed by vacuum distillation, affording almost pure 7β-[2-(2-thienyl)-acetylamino]-3-cephem-4-carboxylic acid p-nitrobenzyl ester as a foam.

Provenance & Evidence