Sodium Bicarbonate → HCID 86752011, compound

Participants

Reaction Steps

1.44 g of (2S,4S)-2-[4-(imidazol-1-yl)piperidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (1) above] were dissolved in a mixture of 1.5 ml of anisole and 7.5 ml of trifluoroacetic acid, and 350 μl of trifluoromethanesulfonic acid were added to the resulting solution, whilst ice-cooling. The resulting mixture was then stirred at room temperature for 1 hour and then at 35° C. for 30 minutes, after which it was concentrated by evaporation under reduced pressure. The resulting residue was washed with diethyl ether four times to give a colorless powder. The whole of this powder was suspended in ethyl acetate, and the suspension was made alkaline by the addition of an aqueous solution of sodium hydrogencarbonate. The ethyl acetate phase was separated and washed with an aqueous solution of sodium chloride, after which this phase was dehydrated over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1150 mg of the title compound, as a colorless powder.

Provenance & Evidence