Triethylamine → Methyl 4-[(2-ethoxy-2-oxoethyl)amino]-4-oxobutanoate

Participants

Reaction Steps

To a suspension of glycine ethyl ester hydrochloride (5.00 g, 35.8 mmol) in tetrahydrofuran (300 mL) were added triethylamine (9.99 mL, 71.6 mmol) and methyl 4-chloro-4-oxobutyrate (5.39 g, 35.8 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by recrystallization (ethyl acetate/hexane) to give the title compound (5.05 g, yield 65%).

Provenance & Evidence