Triethylamine → Ethyl 3-(ethoxycarbonylmethylamino)propionate

Participants

Reaction Conditions

Reaction Steps

150 g of glycine ethyl ester hydrochloride (1.07 mol) was mixed with 1.200 L of ethanol. To this mixture, 110 mL of ethyl acrylate (1.02 mol) was added at an internal temperature of 2 to 25° C. 150 mL of triethylamine (1.08 mol) was then added dropwise at an internal temperature of 20 to 21° C. over 5 minutes. Subsequently, the mixture was stirred at an internal temperature of 23 to 27° C. for 8.5 hours and was allowed to stand overnight. The insoluble material was separated by filtration and the filtrate was evaporated under reduced pressure. 300 mL of ethyl acetate was added to the resulting residue and the insoluble material was separated by filtration and washed with 50 mL of ethyl acetate. The filtrate and the wash were combined and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (533 Pa, 130° C.) to give 138 g of the title compound as a colorless oil (67% yield).

Provenance & Evidence