Ethylmorpholine → N-(3-Hydroxypyridine-2-carbonyl)glycine methyl ester

Participants

Reaction Steps

3-Hydroxypyridine-2-carboxylic acid (6.96 g, 50 mmol), 6.28 g of glycine methyl ester hydrochloride, 6.4 ml of N-ethylmorpholine and 13.53 g of 1-hydroxy-1H-benzotriazole were suspended in 300 ml of anhydrous dichloromethane and a solution of 10.83 g of DCC (=N,N'-dicyclohexylcarbodiimide) in 50 ml of dichloromethane was added to this suspension at 0° C. After 12 hours, the mixture was filtered and the filtrate was washed with water and with a saturated aqueous solution of NaHCO3. Drying and concentrating yielded 7.33 g (70%) of N-(3-Hydroxypyridine-2-carbonyl)glycine methyl ester, m.p. 59°-61° C. (ethyl acetate/heptane), cf. example 1c) as well.

Provenance & Evidence