L-Pyroglutamic Acid → HCID 178516172, compound

Participants

Reaction Steps

A suspension of 12.9 g (0.1 mol) 5-oxo-L-proline, 7.7 ml (0.1 mol) dimethylformamide, and 150 ml of dichloromethane is stirred at 0°-5° C. and 7.3 ml (0.1 mol) of thionyl chloride is added. The reaction mixture is stirred at 0°-5° C. for 1/2 hrs and at room temperature for 2 hrs. After stirring for 20 minutes at room temperature a solution of 11.55 g (0.05 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 7.7 ml (0.55 mmol) triethylamine, and 150 ml of dimethylformamide is added and stirred at 0°-5° C. for 1 hr and at room temperature overnight. The reaction mixture is filtered and the solid is washed with dichloromethane, methanol, water, methanol, and ether to give 13.3 g of 2-[4-[(5-oxo-L-prolyl)amino]phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp>300° C.

Provenance & Evidence