Ammonia → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To 10 ml of nitromethane were added 2.72 g of of 7-amino-cephalosporanic acid (hereinafter referred to as "7-ACA"), 9.63 g of zinc chloride and 0.71 g of methanol. The mixture was heated at 60° C. for 90 min to advance a reaction. After completion of the reaction, the reaction mixture was cooled to 5° C. To the reaction mixture were added 30 ml of water and 10 ml of methanol. Then, the mixture was adjusted to pH 7.8 with aqueous ammonia at a temperature of from -2° C. to 2° C. The resulting precipitate was filtered off, and then washed with water. The filtrate was combined with the washings. The resulting mixture was adjusted to pH 3.5 with 36 % hydrochloric acid to thereby form a precipitate. The precipitate was collected by filtration, and washed with 10 ml of cold water and, then, with 20 ml of cold methanol to obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.98 g. The yield of the desired product was 40 %.

Provenance & Evidence