Diisopropylethylamine → HCID 178484700, compound

Participants

Reaction Steps

N—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N-methylglycine (304 mg, 0.63 mmol) and (3-aminopropyl)(triphenyl)phosphonium bromide hydrobromide (209 mg, 0.63 mmol) were taken up in methylene chloride (3.0 mL) and treated with N,N-diisopropylethylamine (340 μL, 1.96 mmol) and 1-hydroxybenzotriazole hydrate (101 mg, 0.66 mmol). After all the solids dissolved, the reaction as treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (375 mg, 1.96 mmol) and stirred at room temperature overnight. The reaction was diluted with methylene chloride, and the organic layer was washed with aqueous sodium bicarbonate and water and then dried over anhydrous sodium sulfate. After filtration, concentration of the organic gave crude N2—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide (390 mg) in a 68% yield, which was used crude in the subsequent step.

Provenance & Evidence