Dimethyl Sulfoxide → HCID 88868832, compound

Participants

Reaction Steps

Oxalyl chloride (0.31 g, 2.5 mmol) was dissolved in dichloromethane (5 mL), and a solution of dimethyl sulfoxide (0.18 g, 2.3 mmol) in dichloromethane (4 mL) was added dropwise at −78° C., followed by stirring at the same temperature for 15 minutes. To the reaction solution was added dropwise a solution of ethyl({[5-(benzyloxy)-2-{(1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (1.0 g, 1.6 mmol) obtained in Example 1-(11) in dichloromethane (26 mL), followed by stirring at the same temperature for 25 minutes, and subsequently triethylamine (1.1 mL, 8.2 mmol) was added dropwise, and the temperature was raised to room temperature over 1.5 hours. Water was added to the reaction solution, followed by extraction with dichloromethane, and subsequently the extract was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: dichloromethane/ethyl acetate) to afford the title compound (0.85 g, 1.4 mmol) as a yellow solid (yield 85%).

Provenance & Evidence