4-Nitrobenzoic Acid → HCID 86727200, compound

Participants

Reaction Steps

To a solution of tert-butyl((1S,2R,3R,4R,6S)-2,3-bis(benzyloxy)-4-((benzyloxy)methyl)-6-hydroxycyclohexyl)carbamate (3.20 g, 5.85 mmol), triphenylphosphine (1.92 g, 7.31 mmol) and 4-nitrobenzoic acid (1.37 g, 8.19 mmol) in anhydrous THF (50 mL), at 0° C., was added DIAD (1.42 g, 7.02 mmol) slowly. After addition the mixture was stirred at room temperature for 3 h. The solvent were evaporated under reduced pressure, and the residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:10 to 1:3), affording the title compound as a white solid (2.80 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.26-8.20 (m, 4H), 7.33-7.25 (m, 15H), 4.90-4.86 (m, 3H), 4.71 (d, J=11.3 Hz, 1H), 4.57 (d, J=10.8 Hz, 1H), 4.45 (s, 2H), 4.24 (d, J=9.7 Hz, 1H), 3.97-3.93 (m, 1H), 3.68-3.63 (m, 2H), 3.49 (dd, J=2.0, 8.8 Hz, 1H), 3.38 (t, J=10.1 Hz, 1H), 2.22-2.17 (m, 1H), 1.84-1.76 (m, 2H), 1.28 (s, 9H).

Provenance & Evidence