Methanol → HCID 70663440, compound

Participants

Reaction Steps

To a suspension of methyl 3-(3-((4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)(methyl)-carbamoyl)-5-(trifluoromethyl)phenylthio)propanoate (0.2 g, 383 μmol, Example 225) in MeOH (6 mL) and water (0.5 mL) at 0° C. was added Oxone® (588 mg, 957 μmol) and the colorless mixture was stirred at room temperature for 1.75 hours. The white suspension was poured on saturated aqueous NH4Cl solution and EtOAc. The two layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed with 10% aqueous sodium thiosulfate solution and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless foam (0.165 g; 77%). MS (ESI): m/z=555.12 [M+H]+.

Provenance & Evidence