Triethylamine → HCID 17962036, compound

Participants

Reaction Steps

To a solution of 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propionic acid (14.4 g, 35 mmol) and triethylamine (4.9 ml, 35 mmol) in tetrahydrofuran (150 ml) was added ethyl chloroformate (3.4 ml, 35 mmol) followed by stirring for 20 minutes under ice-cooling. To the reaction mixture was added a solution of sodium azide (2.3 g, 35 mmol) in water (30 ml) under ice-cooling. The mixture was stirred under ice-cooling for 20 minutes and then at room temperature for 20 minutes. To the reaction mixture was added ice-cold water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, and filtered. To the filtrate was added methanol, and the mixed solution was concentrated in vacuo. To the residue was added methanol (150 ml), and the mixture was stirred under reflux for 1.5 hours. The reaction mixture was concentrated in vacuo to give methyl N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]carbamate (15.6 g) as a colorless solid.

Provenance & Evidence