Acetone → HCID 59570999, compound

Participants

Reaction Steps

A mixture of (4R)-4-benzyl-3-{2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoyl}-1,3-oxazolidin-2-one (70 g), 4 M hydrochloric acid (140 mL), and acetone (560 mL) was stirred under heating and reflux for 2 hours. After leaving it to be cooled at room temperature, saturated aqueous sodium hydrogen carbonate solution/water (1/1, 200 mL) was added thereto, and the organic solvent was evaporated under reduced pressure, followed by extraction with ethyl acetate (200 mL×2). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70→50:50) to obtain (4R)-4-benzyl-3-{(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoyl}-1,3-oxazolidin-2-one (21 g) as a colorless amorphous substance.

Provenance & Evidence