Sodium Hydroxide → HCID 118377835, compound

Participants

Reaction Steps

To a solution of (1S,2S,3S,4R,5S)-5-[4-chloro-3 [(4-ethoxyphenyl)methyl]phenyl]-1-(1-hydroxy-3-trimethysilyl-prop-2-ynyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 4b (0.44 g, 0.82 mmol) in anhydrous methanol (20 mL) was added sodium hydroxide (32.9 mg, 8.2 mmol). The mixture was stirred at room temperature for 10 hours. The reaction mixture was adjusted to pH 6-7 with saturated aqueous ammonium chloride, and extracted with ethyl acetate (40 mL×3). The combined organic layers were washed with water (30 mL×2) and then saturated aqueous sodium chloride (20 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by prep-HPLC to give the title compound 4 (56 mg, 14.7%, HPLC: 84.2%) as colorless oil. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 461.1[M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.41 (m, 2H), 7.31 (m, 1H), 7.09 (d, 2H), 6.83 (d, 2H), 5.69 (d, 1H), 5.37 (d, 1H), 5.06 (d, 1H), 4.97 (d, 1H), 4.45 (m, 2H), 3.97 (m, 5H), 3.81 (s, 1H), 3.77 (d, 1H), 3.76 (t, 1H), 3.51 (m, 1H), 1.29 (t, 3H).

Provenance & Evidence