Ceric ammonium nitrate → HCID 69939660, compound

Participants

Reaction Steps

A solution of CAN (1.259 g, 2.30 mmol) in water (12 mL) was added to a stirred solution of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylglycyl}-N-(5-chloro-2-{3,3,3-trifluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide (0.798 g, 1.15 mmol) in CH3CN (20 mL) at 0° C. and the resulting solution was warmed to ambient temperature. The solution was partitioned between EtOAc and 10% aqueous NH4OH and the resulting two phase suspension was filtered and the organic layer was washed with 10% sodium sulfite and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica (eluting with 1-10% of 10% ammonium hydroxide in methanol/chloroform gradient) to give N-[2-(2-amino-3,3,3-trifluoropropyl)-5-chlorobenzyl]-1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-prolinamide (0.282 g) as a foam; MS m/z=589.6.

Provenance & Evidence