Water → 5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic Acid 3-benzyloxycarbonyl-phenyl Ester

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(2-adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid (Example 93) (57 mg, 0.16 mmol) and 1,1′-carbonyldiimidazole(25 mg, 0.16 mmol) in DMF (0.5 ml) was stirred at room temperature for 30 min. 3-Benzyloxycarbonyl-phenol (36 mg, 0.16 mmol) was added and the mixture was stirred at 115° C. for 16 h, then cooled to room temperature. Water (5 ml) was added and the mixture was extracted with ethyl acetate (3×5 ml). The combined extracts were washed with brine, dried (MgSO4) and the solvent was evaporated. The crude product was purified by flash chromatography (silica, DCM/ethyl acetate 9:1) to afford colourless foam (15 mg, 17%). 1H NMR (300 MHz, CDCl3) 7.97 (1H, m), 7.91 (1H, m), 7.39 (4H, m), 5.37 (2H, s), 3.01 (2H, m), 2.52 (3H, s), 1.94 (3H, br s), 1.66 (6H, m), 1.54 (8H, m).

Provenance & Evidence