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

Participants

Reaction Steps

2-(Mesityloxy)-2-methylpropionic acid (4.45 g; 20 mmol), diisopropylethylamine (12.93 g; 100 mmol), tert-butyl amino(imino)methylcarbamate (3.82 g; 24 mmol), and 1-hydroxybenzotriazole monohydrate (3.68 g; 24 mmol) were dissolved in N,N-dimethylformamide (100 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (9.10 g; 24 mmol) was added, and the mixture was stirred for 41 hours at room temperature. To the reaction solution, ethyl acetate (300 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution, and then brine. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure. The resulting crystals were dispersed in diisopropyl ether, collected by filtration and dried to give 4.82 g of the title compound (yield 66%).

Provenance & Evidence