Pivaloyl chloride → HCID 10840224, compound

Participants

Reaction Conditions

Reaction Steps

924 mg of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid were dissolved in 10 ml of dry tetrahydrofuran, and the resulting solution was cooled to -20° C. 209 mg of triethylamine, followed by 250 mg of pivaloyl chloride, were then added to the solution, after which the mixture was stirred at the same temperature for 5 minutes. At the end of this time, a mixture of 651 mg of (3S)-3-dimethylaminopyrrolidine trifluoroacetate, 560 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 1 hour. After this, the reaction mixture was filtered, and the solvent was removed by evaporation under reduced pressure. The resulting residue was diluted with ethyl acetate, and the diluted solution was washed with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 3:1 by volume mixture of acetonitrile and methanol as the eluent, to obtain 884 mg of the title compound as a powder.

Provenance & Evidence