Tetrahydrofuran → HCID 118377820, compound

Participants

Reaction Steps

To a solution of 2-amino-1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethanol 10b (50 mg, 0.07 mmol, obtained from the synthetic method described in step 2 of example 10) in tetrahydrofuran (10 mL) was added N,N′-carbonyldiimidazole (14.3 mg, 0.09 mmol) at room temperature. The mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with water (5 mL) and extracted with ethyl acetate (20 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 and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 27a as a white solid (36 mg, 69.5%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.42 (m, 1H), 7.34 (m, 12H), 7.20 (m, 3H), 7.10 (m, 2H), 6.91 (m, 2H), 6.78 (m, 2H), 5.46 (s, 1H), 4.95 (t, 2H), 4.84 (t, 2H), 4.30 (dd, 2H), 4.22 (d, 1H), 4.11 (m, 1H), 4.02 (m, 5H), 3.85 (d, 1H), 3.70 (d, 1H), 3.54 (m, 2H), 3.36 (d, 1H), 1.45 (t, 3H).

Provenance & Evidence