Sulfuric Acid → HCID 178483101, compound

Participants

Reaction Conditions

Reaction Steps

Two and a half grams of 9-amino-6-demethyl-6-deoxytetracycline hydrochloride is added in portions, at 15°-20° C., to a solution of 17 ml of dimethylformamide and 0.6 ml of concentrated sulfuric acid. The added solid is completely in solution after 15 minutes. The solution is then cooled to 0° C. and 2.3 g of chloroacetic anhydride in 5 ml of dimethylformamide is added, dropwise, while maintaining the temperature at 0°-2° C. The reaction mixture is stirred for 30 minutes, poured into 40 g of ice and 35 ml of water, and the pH is adjusted to pH 5.34 with concentrated ammonium hydroxide. The resulting solid is stirred for 30 minutes, collected, washed 2× with water, washed 2× acetone and dried in vacuo to give 2.4 g of the desired intermediate.

Provenance & Evidence