O-Benzylhydroxylamine → HCID 13242803, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-benzyl-acrylic acid (8.0 g, 55 mmol) and O-benzylhydroxylamine (16.0 g, 130 mmol) was heated at 80° C. for 18 hours. The reaction mixture was cooled, diluted with diethyl ether (100 mL) and extracted with 1 M sodium carbonate (3×100 mL). The combined aqueous extracts were acidified with 3 M citric acid and then re-extracted with DCM (3×100 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 2-(R,S)-benzyl-3-benzyloxyamino-propionic acid as a white crystalline solid (7.82 g, 53%). 1H-NMR; δ (CDCl3), 7.61-7.15 (10 H, m), 4.66 (2 H, d, J=1.7 Hz), 3.13-2.94 (4 H, m), 2.84-2.74 (1 H, m).

Provenance & Evidence