Ceric ammonium nitrate → HCID 69939192, compound

Participants

Reaction Steps

A solution of CAN (0.274 g, 0.50 mmol) in water (2.0 mL) was added to a stirred solution of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylglycyl}-N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide (0.168 g, 0.25 mmol) in CH3CN (3.0 mL) at 0° C. and the resulting solution was warmed to ambient temperature. After 18 h the solution was partitioned between EtOAc(20 mL) and 10% aqueous NH4OH (10 mL). 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 chromatography (eluting with 5% methylene chloride, 70% ethyl acetate/hexanes followed by ammonium hydroxide/methanol/chloroform, 1:9:90) to give N-[2-(2-amino-3,3-difluoropropyl)-5-chlorobenzyl]-1-{(2R)-2-[(tert-butoxycarbonyl)amino]2-cyclohexylethanoyl}-L-prolinamide (0.0801 g) as an oil; MS m/z=571.4.

Provenance & Evidence