2-Iodoxybenzoic acid → HCID 117929159, compound

Participants

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 19a (3.48 g, 4.8 mmol, purchased from Shanghai Caerulum Pharma Discovery Co., Ltd.) in dichloromethane (100 mL) was added 2-iodoxybenzoic acid (2.68 g, 9.6 mmol) at room temperature. The mixture was refluxed for 16 hours and filtered. The filtrate was partitioned and the organic layer was adjusted with saturated aqueous sodium bicarbonate to pH 7. The mixture was extracted with dichloromethane (250 mL×2). The combined organic layers were washed with water (100 mL×2) and saturated brine (100 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 19b as yellow oil (3 g, 86.4%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.79 (s, 1H), 7.50 (m, 3H), 7.25 (m, 13H), 7.02 (d, 1H), 6.95 (m, 1H), 6.87 (d, 1H), 6.81 (m, 2H), 4.71 (m, 4H), 4.29 (m, 1H), 4.17 (m, 1H), 4.00 (m, 5H), 3.75 (m, 3H), 3.41 (m, 1H), 1.29 (t, 3H).

Provenance & Evidence