1,2-Dichlorobenzene → HCID 117986007, compound

Participants

Reaction Steps

To a solution of 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]ethane-1,2-diol 7b (0.9 g, 1.22 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 15 mL) were added o-dichlorobenzene (0.82 mL, 6.1 mmol) and 10% Pd/C (36 mg, 0.12 mmol) in turn. The mixture was stirred at room temperature under H2 for 5 hours and filtered. The filter cake was washed with a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL×2). The combined filtrates were concentrated in vacuo. The residue was purified by prep-HPLC to give the title compound 7 as a white solid (94 mg, 9.43%, HPLC: 99.2%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 467.3[M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.40 (m, 2H), 7.29 (dd, 1H), 7.09 (d, 2H), 6.83 (m, 2H), 5.27 (d, 1H), 4.95 (d, 1H), 4.89 (d, 1H), 4.88 (d, 1H), 4.55 (t, 1H), 4.00 (m, 5H), 3.66 (m, 3H), 3.45 (m, 2H), 3.37 (m, 2H), 1.30 (t, 3H).

Provenance & Evidence