2-Oxazolidinone → HCID 9927109, compound

Participants

Reaction Steps

A solution of (S)-N-[[3-[3-fluoro-4-(3-hydroxy-1-azetidinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (EXAMPLE 2, 0.440 g, 1.36 mmol) in 10% acetonitrile/dichloromethane (100 mL) was treated with powdered 4 angstrom molecular sieves (0.682 g), 4-methylmorpholine N-oxide (0.319 g, 2.72 mmol) and then tetra-n-propylammonium perruthenate (0.024 g, 0.068 mmol) at ambient temperature. After stirring 1.5 hours at ambient temperature, TLC analysis (10% methanol/chloroform) revealed a small amount of starting alcohol still remained. The addition of more 4-methylmorpholine N-oxide did not consume the starting material. The reaction mixture was concentrated under reduced pressure to a dark purple solid which was then chromatographed over silica gel (20 g), eluting with a gradient of 1-3.5% methanol/chloroform, to afford, after concentration of appropriate fractions, 0.204 g (47%) of the title oxazolidinone antibacterial agent as a white solid with mp 192°-193° C. and MS(EI) 321 (M+).

Provenance & Evidence