Triethylamine → [(S)-1-(6-Bromo-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl)-ethyl]-methyl-carbamic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-(benzyloxycarbonyl-methyl-amino)-propionic acid (2.7 g, 11.4 mmol) in 10 mL of CH2Cl2 at 0° C., is added 1-chloro-N,N-2-trimethyl-1-propenylamine (1.5 g, 11.4 mmol) drop wise. After being stirred at 0° C. for 20 minutes, the solution is added to a solution of 3-amino-6-bromo-1H-pyridin-2-one (1B) (1.8 g, 9.5 mmol) in 40 mL of CH2Cl2 at 0° C. slowly. Triethyl amine (3.2 ml, 22.8 mmol) is then added slowly. The reaction mixture is stirred at 0° C. for 1 hour, then washed with 2×15 ml of water, and concentrated. The crude product is purified by chromatography (CH2Cl2 95%, MeOH 5%) to give [(S)-1-(6-bromo-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl)-ethyl]-methyl-carbamic acid benzyl ester (1C) (3.0 g, yield 79%) as purple solid. MS (ESI) m/e 408, 410 (M+H+).

Provenance & Evidence