Methanol → HCID 178496801, compound

Participants

Reaction Steps

Into a mixture of each 5 ml of methanol and water was dissolved 114 mg of the crude (-)-N-[4-(3-benzyloxycarbonylaminopropyl)benzyloxycarbonylaminobutyl]-2-(7-guanidino-2-heptenamido)-2-methoxyethanamide hydrochloride obtained above in (a). To the resulting solution were added 0.32 ml of 1N hydrochloric acid and 50 mg of 10% palladium-carbon. The mixture was stirred under a hydrogen stream for 1.5 hours at room temperature. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was passed through a column of 100 ml of CM-Sephadex®C-25 (Na-type) and fractionated by the gradient elution method with each 500 ml of water and 1M aqueous sodium chloride solution (fraction size, 10 g). Fractions No. 69 to No. 74 were combined, concentrated under reduced pressure and extracted three times with 5 ml of methanol. The methanol layer was passed through a column (150 ml) of Sephadex®LH-20 and eluted with methanol to effect desalting (fraction size, 5 g). Fractions No. 16 to No. 21 were combined and evaporated to dryness to obtain 17.4 mg of a white powder of (-)-N-[4-(3-aminopropyl)aminobutyl]-2-(7-guanidinoheptanamido)-2-methoxyethanamide trihydrochloride; overall yield, 16.7%; [α]D25 -30.4° (c 1, water).

Provenance & Evidence