1H-1,2,4-Triazole → HCID 86752015, compound

Participants

Reaction Conditions

Reaction Steps

1.13 g of (2S, 4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid were dissolved in 11 ml of dry tetrahydrofuran, and the resulting solution was cooled to 0° C. 280 mg of triethylamine were added to the solution, followed by 320 mg of pivaloyl chloride, and the mixture was stirred at the same temperature for 5 minutes. At the end of this time, a mixture of 1.36 g of 3-(1-1,2,4-triazolyl)azetidine hydrochloride [prepared by a procedure similar to that described in Preparation 122(a) and (b), but using 1,2,4-triazole], 956 mg of diisopropylethylamine and 6 ml of dry acetonitrile was added to the mixture, after which the mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes. The reaction mixture was then filtered, and the solvent was removed by evaporation under reduced pressure. The resulting residue was diluted with ethyl acetate, and the diluted solution as washed with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography, using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 870 mg of the title compound, as a powder.

Provenance & Evidence