Hydrochloride methanol → HCID 178496807, compound

To a solution of 45.5 mg (0.10 mmole) of N-[4-(3-aminopropyl)aminobutyl]-2-(4-guanidinobutanamido)-2-hydroxyethanamide trihydrochloride in 1 ml of anhydrous methanol was added 0.1 ml of 2N hydrogen chloride-methanol. The mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure and dissolved in 3 ml of water. The resulting solution was passed through a column (20 mm inner diameter) packed with 150 ml of CM-Sephadex® C-25 and fractionated by the gradient elution method with each one liter of water and 1M aqueous sodium chloride solution (17 ml fraction size). The fractions No. 67 to No. 71 corresponding to the salt concentrations of 0.63-0.67M were combined, evaporated to dryness and extracted three times with 5 ml of methanol. The methanol layer was passed through a column (20 mm inner diameter) packed with 150 ml of Sephadex® LH-20 and developed with methanol (7 ml fraction size). Fractions No. 10 to No. 14 were combined and evaporated to dryness, yielding 31.4 mg (67% yield) of a white powder of N-[4-(3-aminopropyl)aminobutyl]-2-(4-guanidinobutanamido)-2-methoxyethanamide trihydrochloride.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutiondissolved in 3 ml of water
3. washfractionated by the gradient elution method with each one liter of water and 1M aqueous sodium chloride solution (17 ml fraction size)
4. customevaporated to dryness
5. extractionextracted three times with 5 ml of methanol
6. customevaporated to dryness

ORD record

ord-20ed408ead504e559fb922b2c467c145

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04983328