Ceric ammonium nitrate → 1-((2R)-2-Cyclohexyl-2-hydroxyethanoyl)-N-(2-(1-amino-2,2-difluoroethyl)-5-chlorobenzyl)-L-prolinamide

Participants

Reaction Steps

A solution of CAN (0.0647 g, 0.12 mmol) in water (0.4 mL) was added to a stirred solution of N-(5-chloro-2-{2,2-difluoro-1-[(4-methoxyphenyl)amino]ethyl}benzyl)-1-[(2R)-2-cyclohexyl-2-hydroxyethanoyl]-L-prolinamide (0.0332 g, 0.06 mmol) in CH3CN (1.5 mL) at 0° C. and the solution was warmed to ambient temperature. After 4 h the solution was partitioned between EtOAc and 10% aqueous NH4OH. The resulting two phase suspension was filtered and the EtOAc layer was washed with 10% sodium sulfite solution and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography on silica (eluting with 1-10% of 10% ammonium hydroxide in methanol/chloroform gradient) to give the title compound as a gum: LC-MS m/z=458.4.

Provenance & Evidence