Chloroacetyl chloride → (S)-2-Chloro-N-(2,3-dihydroxypropyl)acetamide

Participants

Reaction Conditions

Reaction Steps

(S)-3-Amino-1,2-propanediol (16.8 g, 184 mmol) was dissolved in MeOH (90 mL) at room temperature and the solution was diluted with MeCN (550 mL). NEt3 (30.5 mL, 219 mmol) was added and the reaction mixture was cooled to −10° C. Chloroacetyl chloride (22.2 g, 15.6 mL, 197 mmol) was added dropwise at −10° C. during 1.5 h under nitrogen. The temperature was maintained at −10° C. for an additional hour and then the reaction mixture was allowed to reach room temperature and stirred overnight (16 h). The solvents were removed in vacuo. The residue was purified by column chromatography (normal phase, Apollo Scientific silica, 40-60μ, 60 Å, gradient 1% to 10% MeOH in EtOAc). The combined fractions were evaporated to afford 2-chloro-N—[(S)-2,3-dihydroxypropyl]-acetamide (28.5 g, 92%) as a colourless oil which gave a white solid on standing.

Provenance & Evidence