Methanesulfonic Acid → HCID 10111943, compound

Participants

Reaction Steps

To tert-butyl 4-{4′-[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino][1,1′-biphenyl]-4-yl}-1-piperazinecarboxylate (122 mg, 0.242 mmol) in dry TB (5 mL) under dry nitrogen was gradually added a total of 10 equivalents of MeSO3H (160 μL, 2.42 mmol) over a period of 5 days in portions of 1–2 equivalents at a time. Aqueous sat. NaHCO3 was added carefully and the product was extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1.5/13.5/85) to afford (2S)-N-(cyanomethyl)-4-methyl-2-{[4′-(1-piperazinyl)[1,1′-biphenyl]-4-yl]amino}pentanamide. MS (+ESI): 406.9 [M+1]+.

Provenance & Evidence