Sodium hydride → (R)-4-benzyl-3-[2-(4-benzyloxy-3,5-difluoro-phenyl)-cyclopropanecarbonyl]-oxazolidin-2-on

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Reaction Steps

After (R)-4-benzyl-oxazolidin-2-on (52 mg, 0.295 mmol) was dissolved in anhydrous THF (2 ml), NaH (60%, 14 mg, 0.344 mmol) was added thereto, and the mixture was stirred for 30 minutes. Next, 2-(4-benzyloxy-3,5-difluoro-phenyl)-cyclopropanecarnoyl chloride obtained in Step A was added thereto at −78° C., and the mixture was stirred for 15 minutes, and then stirred at room temperature for 1 hour. After the termination of the reaction, NH4Cl solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was separated, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain each title compound [(more polar, 41 mg, 36%), (less polar, 44 mg, 38%)].

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