Water → HCID 23398407, compound

Participants

Reaction Steps

To a solution of N-[(1S, 2S)-2-(benzyloxy)cyclopentyl]-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxamide (Table entry 282, prepared according to the procedures described in Examples 13 and 14) (119 mg, 0.22 mmol) in CH2Cl2 (4 mL), TMSI (0.2 mL, 1.4 mmol) was added. The mixture was stirred at rt overnight, and diluted by water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by preparative TLC (EtOAc) to afford 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-N-[(1S, 2S)-2-hydroxycyclopentyl]-1H-imidazole-4-carboxamide (80 mg, 82% yield) as a white foam: LC-MS m/z 450.0 (MH+), retention time 3.24 min (method 1); Rf=0.45 (50% EtOAc in hexane); 1H NMR (300 MHz, CDCl3) δ 1.22-2.24 (6H, m), 3.97-4.15 (2H, m), 7.03-7.42 (7H, m), 7.86 (1H, s).

Provenance & Evidence