4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester → 4-{3-[(1,4-dimethyl-1H-indol-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}pentanoic acid

Participants

Reaction Steps

To a solution of 4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester (120 mg, 0.3 mmol) in dioxane (2.5 ml) was added a solution of LiOH monohydrate (25 mg, 0.6 mmol) in H2O (2.5 mL). The solution was stirred at room temperature for 4 hours. The reaction mixture was quenched with 4M HCl in dioxane (250 □L) and concentrated. The resulting residue was purified by CombiFlash with 10% MeOH in dichloromethane as the eluent to afford the desired 4-{3-[(1,4-dimethyl-1H-indol-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}pentanoic acid (17 mg, 15%). LCMS (ESMS): 392.26 (M+H+).

Provenance & Evidence