Atrolactic acid → N-Methyl-N-methoxy-2-hydroxy-3-phenylpropanamide

Participants

Reaction Steps

A solution of 2.0 g (12 mmol) of phenyllactic acid, 1.17 g (12 mmol) of N,O-dimethylhydroxylamine hydrochloride, and 1.78 g (13 mmol) of 1-hydroxybenzotriazole in 20 ml of dimethylformamide was treated sequentially with 2.77 ml (25 mmol) of 4-methylmorpholine and 2.53 g (13 mmol) of N-ethyl-N'-(dimethylaminoethyl)carbodiimide. After being stirred at ambient temperature overnight, the solution was diluted with ethyl acetate; washed sequentially with water, 10% citric acid, aqueous NaHCO3, and saturated brine; dried over MgSO4 ; and concentrated in vacuo to give 2.5 g (100%) of the crude desired compound. 1H NMR (CDCl3) δ 2.85 (dd, J=14, 7 Hz, 1H), 3.08 (dd, J=14, 4 Hz, 1H), 3.23 (s, 3H), 3.72 (s, 3H), 4.62 (m, 1H), 7.2-7.3 (m, 5H). Mass spectrum (M+H)+ =210.

Provenance & Evidence