M-Phenylenediamine → HCID 90052166, compound

Participants

Reaction Steps

To a solution of 2-(tert-butoxycarbonylamino)isobutyric acid (203 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (211 mg) and 1-hydroxybenzotriazole monohydrate (149 mg) in N,N-dimethylformamide (3 mL), N,N-diisopropylethylamine (510 μL) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. To the reaction mixture, a solution of 1,3-phenylenediamine (260 mg) in N,N-dimethylformamide (2 mL) was added at room temperature, and the mixture was stirred at 80° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl (1-((3-aminophenyl)amino)-2-methyl-1-oxopropan-2-yl)carbamate (B8, 195 mg) as white solid.

Provenance & Evidence