Pivaloyl chloride → HCID 67585187, compound

Participants

Reaction Conditions

Reaction Steps

768 mg of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid were dissolved in 8 ml of dry tetrahydrofuran, and the resulting solution was cooled to 0° C. 191 mg of triethylamine were added to the solution, followed by 218 mg of pivaloyl chloride, and then the mixture was stirred at the same temperature for 5 minutes. At the end of this time, a mixture of 238 mg of (3S)-3-(1-1,2,4-triazolyl)pyrrolidine trifluoroacetate, 440 mg of diisopropylethylamine and 7 ml of dry acetonitrile was added to the mixture, and the mixture was gradually heated and then stirred at 0° C. for 15 minutes and at room temperature for 2 hours. The solvent was then removed by evaporation under reduced pressure, and the residue was diluted with ethyl acetate, after which the diluted solution was 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 7:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 803 mg of the title compound, as a powder.

Provenance & Evidence