Sodium Carbonate → 1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-methylbutyl)-1H-1,2,3-triazole-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-methyl-3-oxoheptanoate (1.08 g, 5.53 mmol, 1.25 eq.) obtained in Example 97a) and 4-azido-N-ethylbenzamide (0.842 g, 4.43 mmol) were dissolved in ethanol (25 ml), sodium ethoxide (418 mg, 5.53 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 60° C. for 17 hr. 2% Aqueous sodium carbonate solution (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with water (20 ml) and washed with ethyl acetate-hexane (2:1, 40 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid, and stood still at 0° C. The precipitate was collected by filtration and washed with cold water and dried to give the title compound as a grayish white powder (1.41 g, 4.27 mmol, 96.3%).

Provenance & Evidence