Sodium Carbonate → HCID 21308235, compound

Participants

Reaction Steps

A solution of (S)-N-[[3-[4-[3-[(tert-butyldimethylsilyl)oxy]-3-methyl-1-azetidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.550 g, 1.22 mmol) in acetonitrile (20 mL) in a polypropylene bottle was treated with 40% aqueous hydrofluoric acid (5 mL) at ambient temperature. After 16 h TLC analysis (5% methanol/chloroform) revealed the deprotection was essentially complete. The reaction mixture was transferred to an erlenmeyer flask along with some dichloromethane (150 mL). The stirred mixture was carefully treated with saturated aqueous sodium carbonate (300 mL, gas evolution). After gas evolution ceased, the mixture was transferred to a separatory funnel and the phases separated. The aqueous phase was neutralized to pH 7 by the addition of 6N hydrochloric acid and extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. Radial chromatography over silica gel, eluting with 5% methanol/chloroform, afforded, after concentration of appropriate fractions, 0.374 g (91%) of the title oxazolidinone antibacterial agent as a white solid with mp 152°-153° C. and MS(EI) 337 (M+).

Provenance & Evidence