Hydrochloric Acid → HCID 118377790, 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-3-fluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]methanol 20a (1.0 g, 1.38 mmol, purchased from Shanghai Caerulum Pharma Discovery Co., Ltd.) in tetrahydrofuran (20 mL) were added saturated aqueous sodium bicarbonate (20 mL), potassium bromide (33 mg, 0.28 mmol) and 2,2,6,6-tetramethylpiperidinooxy (22 mg, 0.14 mmol) in turn at 0° C., and then sodium hypochlorite (18 mL, available chlorine ≧5.5%) was added dropwise over a period of 20 min. The mixture was stirred at 0° C. for 40 min and acidified with aqueous HCl (1 N) till pH becomes 4. The resulting mixture was extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with saturated brine (20 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 20b (1.20 g, 117.6%) as yellow oil. This material was not further purified.

Provenance & Evidence