Hydrochloric Acid → N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucine

Participants

Reaction Steps

To methyl N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinate (375 mg, 0.793 mmol) in MeOH (20 mL) was added an aqueous solution of LiOH (2.0 M, 2.0 mL, 4.0 mmol) and the reaction mixture was stirred for 2 hours. An additional aliquot of aqueous LiOH (2.0 M, 2.0 mL, 4.0 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was acidified (pH=4–5) with aqueous 10% HCl, brine was added and the product extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (Hex/EtOAc/AcOH, 50/49/1) to afford N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucine.

Provenance & Evidence