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

Participants

Reaction Conditions

Reaction Steps

4.1 ml of concentrated sulfuric acid was added to 80 me of sulfolane and the resulting mixture was cooled to about 0° C. 8.2 ml of trimethyl borate was added dropwise thereto and 10 g of 7-aminocephalosporanic acid was added thereto in small portions. 8.4 ml of antimony pentachloride was added dropwise thereto at about 0° C., stirred at 0 ° C. for additional 6 hours, and then, the resulting mixture was added to ice-water. The pH of the mixture was adjusted to 3.4 with aqueous ammonia. The ocherous solid formed was isolated by filtration and washed with water. The wet solid was dispersed in water and the pH of the resulting mixture was adjusted to 8 with aqueous ammonia to dissolve the solid in water, and then, the pH of the resulting mixture was adjusted to 3.5 with 3N hydrochloric acid. The resulting mixture was filtered to obtain crystals which were washed with water, and then, dried overnight in a vacuum to give 1.75 g of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid as an ocherous solid (Yield: 20% and Purity: 94.3%). H-NMR data was equal to that of the compound prepared in Example 1.

Provenance & Evidence