Sodium hydride → HCID 69363345, compound

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Reaction Steps

Sodium hydride (60% in oil, 148 mg, 3.7 mmol) was suspended in dry N,N-dimethylformamide (5 ml) and 1,2,3-triazole (0.26 g, 3.7 mmol) was added under nitrogen. It was stirred for 5 minutes at room temperature and methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester (see Example 86; 1.0 g, 2.47 mmol) was added. It was heated to 75° C. for 3.5 hours, then cooled to room temperature, diluted with aqueous sodium hydrogencarbonate solution (5%, 100 ml) and extracted with ethylacetate (2×100 ml). The organic phase was washed with water (2×50 ml), brine (100 ml), dried over magnesium sulfate and the solvent was evaporated in vacuo. Chromatography on silica gel with a gradient of 10–50% ethylacetate in hexanes gave the title compound (0.65 g). MS (ESP): 379. (MH+) for C17H16F2N4O2S

Provenance & Evidence