Trimethylsilyldiazomethane → Methyl 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoate

Participants

Reaction Steps

To a solution of 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid from Step A (400. mg, 1.46 mmol) in MeOH (3 mL), was added trimethylsilyldiazomethane (2 M in hexanes) until yellow color persists. The reaction mixture was stirred for an additional twenty minutes. The reaction mixture was diluted with ether (30 mL) and water (10 mL). The organics were washed with 5% sodium bicarbonate and then with saturated brine. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue. This residue was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:Hexanes—40:60 to 90:10, to give the title compound. MS: m/z=229 (M−CO2Me).

Provenance & Evidence