Sodium Hydroxide → HCID 178491276, compound

Participants

Reaction Steps

To a solution of 4-fluoro-N-(4-fluorobenzoyl)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-2-yl)benzamide (442 mg, 0.649 mmol, as a mixture with the mono-acylated material) in MeOH (3.2 mL) and dioxane (3.2 mL) was added a flake of sodium hydroxide (46.7 mg, 1.169 mmol), and the mixture was stirred at RT for 1 hour. The mixture was evaporated and the residue diluted with DCM, washed with 1 N aqueous NaOH, brine, and the organic layer dried over Na2SO4. The residue was purified via flash chromatography using a linear gradient of 0% to 50% EtOAc in hexanes. The title compound was collected as a white solid (275 mg, 76% yield). M/Z calc'd for C32H35FN4O4: 558.65. found 559 [M+H].

Provenance & Evidence