1-Hydroxybenzotriazole → HCID 57273518, compound

Participants

Reaction Steps

To a solution of (3S)-3-(pyrrolidin-1-ylmethyl)pyrrolidine hydrochloride (367 mg), which had been prepared from (3R)-1-tert-butoxycarbonyl-3-hydroxymethylpyrrolidine, in anhydrous dimethylformamide (10 ml), (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid (804 mg), diisopropylethylamine (1.16 ml), 1-hydroxybenzotriazole (243 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (483 mg) were added. The resulting mixture was stirred at room temperature for 10 hours. The solvent was then distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate/methanol=5/1-1/1), whereby (2S,4S)-4-(4-methoxybenzylthio)-2-[(3R)-3-(pyrrolidin-1-ylmethyl)pyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (362 mg) was obtained.

Provenance & Evidence