Methyl iodide → HCID 90281977, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-{[(2-tert-butoxy-2-oxoethyl){2-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorophenyl)amino]-2-oxoethyl}amino]methyl}thiophene-2-carboxylate (375 mg) in tetrahydrofuran (7.50 mL) was added 55% sodium hydride (25.2 mg) under ice-cooling, followed by stirring at room temperature for 30 minutes. Iodomethane (0.187 mL) was added thereto at room temperature, followed by stirring at room temperature for 2 hours. To the reaction mixture was added ethyl acetate, and water and a saturated aqueous ammonium chloride solution was added thereto under ice-cooling. The organic layer was extracted, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 4-{[(2-tert-butoxy-2-oxoethyl) {2-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorophenyl)(methyl)amino]-2-oxoethyl}amino]methyl}thiophene-2-carboxylate (209 mg).

Provenance & Evidence