Water → 2(1H)-Pyridinone, 3-((2-(((aminocarbonyl)oxy)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1H-imidazol-1-yl)methyl)-

Participants

Reaction Conditions

Reaction Steps

In 20 ml of tetrahydrofuran was dissolved 200 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(1,2-dihydro-2-oxopyridinylmethyl)-4-isopropyl-1H-imidazole (116b), the mixture was cooled to -40° C. Under stirring, 84 μl of trichloroacetylisocyanate was added, the mixture was allowed to stand to reach room temperature, and stirred for 30 minutes. There were added 500 μl of triethylamine, 5 ml of water and 5 ml of methanol, and the mixture was stirred at 70° C. for 1 hour. After completion of the reaction, the solution was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crystals were washed with diethyl ether, filtered, and 177 mg of Compound I-132 was obtained (yield 80%)mp 214° C.

Provenance & Evidence