Citric Acid → HCID 66990230, compound

Participants

Reaction Steps

Potassium carbonate (0.084 g) and methyl iodide (0.028 mL) were added to an N,N-dimethylacetamide (1.5 mL) solution of tert-butyl 2-(4-amino-2-(benzyloxy)benzamido)-4-phenylbenzoate (0.15 g), followed by stirring at room temperature for 1 hour and then at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.042 g) and methyl iodide (0.019 mL) were added thereto, followed by stirring at 80° C. for 20 minutes. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a 10% aqueous solution of citric acid and a saturated aqueous solution of sodium chloride sequentially, 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: 90-70% hexane/ethyl acetate] to obtain 0.056 g of tert-butyl 2-(2-(benzyloxy)-4-(methylamino)benzamido)-4-phenylbenzoate as a white solid and 0.049 g of tert-butyl 2-(2-(benzyloxy)-4-(dimethylamino)benzamido)-4-phenylbenzoate as a white solid.

Provenance & Evidence