1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86608409, compound

Participants

Reaction Steps

{t-Butoxycarbonyl-[2-(1,3-dihydroisoindol-2-yl)-2-oxoethyl]amino}acetic acid (260 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (150 mg) and hydroxybenzotriazole (120 mg) were dissolved in N,N-dimethylformamide (5.0 ml). Triethylamine (110 μl) and (S)-pyrrolidine-2-carbonitrile hydrochloride (100 mg) were added thereto, and the mixture was stirred for 21 hours at room temperature. The reaction mixture was concentrated under reduced pressure, then ethyl acetate and 10% citric acid solution were added to the residue, and the organic phase was separated. The organic phase was washed with 4% sodium bicarbonate solution and a saturated saline solution and dried over sodium sulfate anhydrous. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (eluting solvent; dichloromethane:methanol 20:1) to give t-butyl (S)-[2-(cyanopyrrolidin-1-yl)-2-oxoethyl]-[2-(1,3-dihydrois oindol-2-yl)-2-oxoethyl]carbamate (290 mg, Y.:90%).

Provenance & Evidence