Methanol → (S)-N-((3-(3-fluoro-4-(1-oxidothiomorpholino)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Participants

Reaction Conditions

Reaction Steps

Sodium metaperiodate (42 mg, 0.196 mmol) was dissolved in water (1 mL) and then cooled to 0° C. (ice bath). Next, the N-[[3-[3-fluoro-4-(4-thiomorpholinyl) phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (66 mg, 0.187 mmol) was added. Methanol (3 mL) was added to increase solubility. The reaction was stirred at 0° C. for an additional 4 hours under N2 before being stoppered and stored in the freezer (65 hours). The reaction was filtered through a medium-porosity sintered glass funnel, rinsing the flask and filter cake with CHCl3 (5 mL). The filtrate was transferred to a separatory funnel, the layers separated, and the water layer further extracted with more CHCl3 (3×5 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and then concentrated under reduced pressure to yield 80 mg of a gummy solid. The material was chromatographed on silica gel (10 g silica, packed with 10% CH3CN/CHCl3), eluting with a gradient of 1-5% MeOH in 10% CH3CN/CHCl3 to give 49 mg (71%) of the title compound as an off-white solid with a mp of 159°-161° C. and a HRMS (M+) calculated for C16H20N3O4FS 369.1158, found 369.1182.

Provenance & Evidence