Benzenesulfonyl chloride → HCID 86590379, compound

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Reaction Steps

To a solution of 5(R)-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]-5-hydroxymethyloxazolidin-2-one (2.55 g) and triethylamine (1.7 mL) in tetrahydrofuran (20 mL) was added benzenesulfonyl chloride (1.2 mL) at 0° C., the mixture was stirred at room temperature overnight, and heated at 40° C. for 10 hours. After dilution with water, the mixture was extracted with tetrahydrofuran. The organic extracts were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave 5(R)-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]-5-phenylsulfonyloxymethyloxazolidin-2-one (3.05 g).

Provenance & Evidence