Sodium Chloride → HCID 24875829, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(2-tetrahydropyranyloxy) cyclopentyl]heptanoate (1) (70.49 g, 124.8 mmol) in acetonitrile (705 ml), water (70.5 ml) and 85% aqueous phosphoric acid (70.5 ml) were added, and the mixture was stirred for three hours at about 20° C. 10% aqueous sodium chloride (705 ml) was added to the mixture and the mixture was extracted with ethyl acetate (276 ml) for 3 times. The organic layers were combined and washed with 10% aqueous sodium chloride (360 ml), saturated aqueous sodium bicarbonate (360 ml) and saturated aqueous sodium chloride (360 ml) successively, dried with anhydrous magnesium sulfate (51 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia BW-300 2100 g, ethyl acetate:hexane=1:4). Fractions containing impurities were purified again by silica gel column chromatography (Fuji Silysia BW-300 1000 g, ethyl acetate:hexane=1:4) to give benzyl 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl]heptanate (2) (52.64 g, 109.5 mmol, yield: 87.8%).

Provenance & Evidence