Hydrochloric Acid → HCID 118377859, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 23n (0.56 g, 0.67 mmol, obtained from the synthetic method described in step 12 of example 23) in tetrahydrofuran (12 mL) were added aqueous sodium bicarbonate (12 mL, 7.4 mmol, 0.6 M), potassium bromide (16 mg, 0.13 mmol) and 2,2,6,6-tetramethylpiperidinooxy (10 mg, 0.07 mmol) in turn at 0° C., and then sodium hypochlorite (9 mL, 10.60 mmol, 3.5% available chlorine) was added dropwise. The mixture was stirred at 0° C. for 2 hours and acidified with aqueous HCl (1 N) till pH becomes 4. The resulting mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 24a (0.6 g, 100%) as yellow oil. This material was not further purified.

Provenance & Evidence