Diisopropylethylamine → tert-butyl N-[N-[(2S)-2-(2,4,6-trimethylphenoxy)propanoyl]carbamimidoyl]carbamate

Participants

Reaction Steps

(2S)-2-(Mesityloxy)propionic acid (5.6 g; 27 mmol), diisopropylethylamine (17.3 g; 133 mmol), tert-butyl amino(imino)methylcarbamate (4.3 g; 27 mmol), and 1-hydroxybenzotriazole monohydrate (4.1 g; 27 mmol) were dissolved in N,N-dimethylformamide (80 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (10.2 g; 27 mmol) was added, and the mixture was stirred for 137 hours at room temperature. To the reaction solution, ethyl acetate (400 mL) was added, and the mixture was washed sequentially with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure, to give 8.6 g of the title compound (yield 91%) as an oil.

Provenance & Evidence