1,2-Dichlorobenzene → HCID 117986065, compound

Participants

Reaction Steps

To a solution of 2-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]propan-2-ol 22c (86 mg, 0.11 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (0.064 mL, 0.57 mmol) and 10% Pd/C (13 mg, 0.01 mmol) at room temperature. The mixture was stirred at room temperature under H2 for 4 hours and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/3 to give the title compound 22 as white oil (43.9 mg, 79.8%, HPLC: 92.7%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 531.0 [M+HCOO]−; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.42 (m, 1H), 7.37 (m, 2H), 6.96 (m, 1H), 6.93-6.85 (m, 1H), 5.51 (d, 1H), 5.05 (d, 1H), 5.00 (d, 1H), 4.24 (s, 1H), 4.05 (m, 3H), 3.85 (s, 3H), 3.79 (d, 1H), 3.75-3.65 (m, 1H), 3.50-3.36 (m, 2H), 1.20 (s, 3H), 1.15 (s, 3H).

Provenance & Evidence