Benzoyl chloride → N-Benzoyl-L-asparagine

Participants

Reaction Steps

To a vigorously stirred solution of 2 g (0.013 mol) of L-asparagine monohydrate and 2.02 g (0.014 mol) of potassium carbonate in 15 ml of water, 1.51 ml (0.013 mol) of benzoyl chloride was added dropwise, over a period of 15 min., at room temperature. The stirring was continued for 2 hour, then the mixture was extracted with 10 ml of ether and the aqueous phase was acidified to pH 2 with concentrated hydrochloric acid. The white precipitate was filtered off, washed with water and purified by crystallization from isopropyl alcohol to give 2.1 g (68% yield) of the title compound at 190-192° C.; NMR (DMSO-d6): 2.62 (m, 2H, CH2); 3.32 (broad s, 1H, OH); 4.72 (m, 1H, CH); 6.64-8.0(m, 7H, aromatic, NH2); 8.6 (d, 1H, NH).

Provenance & Evidence