Acetone → Tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate

Participants

Reaction Steps

Potassium carbonate (0.16 g) and dimethyl sulfate (0.094 mL) were added to an acetone (4.0 mL) solution of tert-butyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate (0.27 g), followed by heating to reflux for 2 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] and then purified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate] to obtain 0.061 g of tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate as a colorless oily substance.

Provenance & Evidence