Ethyl Acetate → US10385022, Example 314

Participants

Reaction Steps

To an ice-cold solution of N-(4-(4-fluoro-2-methoxyphenyl)-6-methylpyridin-3-yl)-N-methyl-3-(oxetan-3-ylthio)-5-(trifluoromethyl)benzamide (0.045 g, 88.8 μmol, example 310) in MeOH (2 mL) and water (0.5 mL) was added Oxone® (137 mg, 222 μmol) and stirring was continued at room temperature for 2.5 hours. The reaction mixture was poured on 10% aqueous Na2S2O3 solution and EtOAc and the layers were separated. The aqueous layer was saturated with sodium chloride, extracted three times with EtOAc. The organic layers were washed once with brine, dried over MgSO4, filtered 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). The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Light brown foam (0.038 g; 79%). MS (ESI): m/z=539.13 [M+H]+.

Provenance & Evidence