1,2-Dichlorobenzene → HCID 117986071, compound

Participants

Reaction Steps

To a solution of 5-[(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]oxazolidin-2-one 27a (113 mg, 0.17 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (0.1 mL, 0.85 mmol) and 10% Pd/C (20 mg, 0.02 mmol) at room temperature. The mixture was stirred at room temperature under H2 for 4 hours and filtered. The filter cake was washed with a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL×2). The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/1 to give the title compound 27 as a white solid (66.2 mg, 78.8%, HPLC: 90.1%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 492.2 [M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.54 (s, 1H), 7.42 (m, 2H), 7.31 (m, 1H), 7.16 (m, 2H), 7.34 (m, 2H), 5.68 (d, 1H), 5.18 (d, 2H), 4.81 (t, 1H), 4.11 (m, 1H), 3.98 (m, 4H), 3.69 (t, 1H), 3.48 (m, 3H), 3.30 (m, 1H), 3.21 (m, 1H), 1.32 (t, 3H).

Provenance & Evidence