Sodium Carbonate → HCID 178452036, compound

Participants

Reaction Steps

To a solution of (3S)-1-(tert-butoxycarbonyl)-3-(aminoacetylamino)pyrrolidine (2.50 g) in water (35 ml), sodium carbonate (1.31 g) and formamidinesulfonic acid (1.53 g) were added under ice cooling and the mixture was stirred overnight at room temperature. To the reaction mixture, tetrahydrofuran (30 ml) was added. To the resulting mixture, a solution of p-nitrobenzyl chloroformate (4.43 g) in tetrahydrofuran (20 ml) and a 1N aqueous sodium hydroxide solution (21 ml) were simultaneously added dropwise, followed by stirring at the same temperature for one hour. To the reaction mixture, ethyl acetate was added. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure, whereby (3S)-1-(tert-butoxycarbonyl)-3-[di(4-nitrobenzyloxycarbonyl)guanidinoacetylamino]pyrrolidine was obtained. The product was provided for the subsequent step.

Provenance & Evidence