Sodium Bicarbonate → N-(cyanomethyl)-N2-[3-methyl-4-(4-piperazin-1-ylphenyl)isoxazol-5-yl]leucinamide

Participants

Reaction Steps

To N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinamide (210 mg, 0.411 mmol) in dry THF (0.5 mL) under dry nitrogen was gradually added a total of 5 equivalents of MesO3H (100 μL, 1.37 mmol) over a period of 3 hours in portions of 1–2 equivalents at a time and the reaction mixture was stirred overnight. Aqueous sat. NaHCO3 was added carefully and the product was extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90) to afford N-(cyanomethyl)-N2-[3-methyl-4-(4-piperazin-1-ylphenyl)isoxazol-5-yl]leucinamide. MS (−ESI): 409.7 [M−1]−.

Provenance & Evidence