Methyl iodide → tert-Butyl {5-[{2-([tert-butoxycarbonyl)(methyl)amino]ethyl}(methyl)carbamoyl]-4-methylthiophen-2-yl}methylcarbamate

Participants

Reaction Steps

Sodium hydride (50 mg, 55%, 1.14 mmol) was added to a solution of the compound (407 mg, 0.952 mmol) obtained in Example 89b in N,N-dimethylformamide (3 mL) under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (0.119 mL, 1.90 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed successively with water (×3) and saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, v/v) to give the title compound (418 mg; yield, 99%) as a white solid.

Provenance & Evidence