Potassium Carbonate → HCID 117985977, compound

Participants

Reaction Steps

To a solution of [(1R,2S,3S,4R,5S)-2,4-diacetoxy-1-(1-acetoxyethyl)-5-[4-chloro-3-[(4-ethoxyphenyl)-hydroxy-methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-3-yl]acetate 29d (316 mg, 0.5 mmol) in methanol (20 mL) was added potassium carbonate (344 mg, 2.5 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. Part of the solvent was removed in vacuo. The residue was extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with water (10 mL×2) and then saturated aqueous sodium chloride (10 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with EtOAc to give the title compound 29 as a white solid (47 mg, 20.0%, HPLC: 99.2%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.84 (s, 1H), 7.32 (d, 2H), 7.19 (d, 2H), 6.84 (d, 2H), 5.93 (d, 1H), 5.90 (d, 1H), 5.31 (d, 1H), 5.02 (d, 1H), 4.91 (d, 1H), 4.65 (d, 1H), 4.04 (m, 1H), 4.01-3.96 (m, 2H), 3.88-3.82 (m, 1H), 3.79 (d, 1H), 3.61-3.55 (m, 1H), 3.46 (d, 1H), 3.44-3.39 (m, 1H), 1.30 (t, 3H), 1.17 (d, 3H); and MS (ESI, pos. ion) m/z: 5112[M+HCOO]−.

Provenance & Evidence