Methanol → HCID 178496801, compound

HRID 462918Notes

Reaction equation

HRID 462918 reaction equation
CO.Cl.[CH2:4]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH:18]([NH:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:40])[CH:24]([NH:27][C:28](=[O:39])[CH:29]=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:38])=[NH:37])[O:25][CH3:26])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O>[CH2:4]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH:18]([NH:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:40])[CH:24]([NH:27][C:28](=[O:39])[CH:29]=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:38])=[NH:37])[O:25][CH3:26])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 178496802HCID 178496802, compound

Product 1

HCID 178496801HCID 178496801, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Sources & evidence

ORD record
ord-11d40813f88f4fbcb3e0103996483f87
Source dataset
uspto-grants-1985_05
Patent number
US04518532

Reaction notes

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