Methanesulfonic Acid → 7beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

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Reaction Steps

To a solution of sodium bicarbonate (9.24 g, 0.11 mol) in water (1 liter) was added 7β-aminocephalosporanic acid (27.2 g, 0.1 mol) and the mixture was stirred until solution results. The sodium salt of 1-amino-5-mercapto-1H-tetrazole (27.8 g, 0.2 mol) was added to the mixture and allowed to react in an argon stream between 52° C. and 53° C. for 3 hours. An additional amount of the sodium salt of 1-amino-5-mercapto-1H-tetrazole (6.95 g, 0.5 mol) was added to the mixture and allowed to react at the same temperature for 2 hours. The mixture was then passed three times through a layer of activated carbon (15 g) in order to decolorize it. The filtrate was adjusted to pH 4.6 with methanesulfonic acid (about 6 ml) under ice-cooling and set aside to precipitate. The precipitated substance was filtered, washed with water and dried in vacuo over phosphorus pentoxide to give ocherous powder of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (17.3 g, 52%), mp~206° C. (decomposition).

Provenance & Evidence