Ammonium Chloride → (S)-[(N-Methoxy-N-methylcarbamoyl)phenylmethyl]carbamic Acid Benzyl Ester

Participants

Reaction Steps

To a solution of Z-L-phenylglycine (5.0 g, 17.5 mmol) in dichloromethane (35 mL) is added 1,1′-carbonyldimidazole (3.13 g, 19.3 mmol), and the solution is stirred at rt for 0.5 h. To the solution is added N,O-dimethylhydroxylamine hydrochloride (1.88 g, 19.3 mmol), and the mixture is stirred at rt overnight. To the reaction mixture is added ammonium chloride solution and EtOAc, and the organic layer is separated, washed with brine, dried (MgSO4), and filtered. The filtrate is evaporated to give 5.65 g of the product 482. 1H NMR (CDCl3) δ 7.50-7.20 (m, 10H), 6.10 (d, 1H), 5.78 (d, 1H), 5.20-5.00 (m, 2H), 3.43 (s, 3H), 3.18 (s, 3H); MS: m/z 329 (M++1).

Provenance & Evidence