Hydrochloric Acid → 7-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

Participants

Reaction Steps

To a suspension of 27.2 g. (0.1 mol.) of 7-ACA in 200 ml. of water and 100 ml. of acetone was added a solution of 18.9 g. of sodium bicarbonate in 200 ml. of water. The resultant solution was warmed on a stream bath and a solution of 14.5 g. (0.125 mol.) of 1-methyl-5-mercapto-1,2,3,4-tetrazole in 200 ml. of acetone was added. The reaction mixture was refluxed for 3.5 hr. while maintaining the pH at 7.4-8.0 by addition of 5% sodium bicarbonate solution. Acidification of the cooled reaction mixture to pH 3.5 with 6N hydrochloric acid resulted in precipitation of 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid which was collected, washed (H2O) and air dried (16 g.; 49%).

Provenance & Evidence