HCID 10424733, compound → HCID 69031029, compound

Participants

Reaction Steps

N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%).

Provenance & Evidence