Methanesulfonic Acid → N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)-1,2,5-oxadiazol-3-yl]leucinamide

Participants

Reaction Steps

To N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinamide (170 mg, 0.33 mmol) in dry THF (1 mL) under dry nitrogen was gradually added a total of 6 equivalents of MeSO3H (120 μL, 2.0 mmol) over a period of 2 hours in portions of 2 equivalents at a time and the reaction mixture stirred overnight. Aqueous sat. NaHCO3 was added carefully and the product 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 N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)-1,2,5-oxadiazol-3-yl]leucinamide.

Provenance & Evidence