Acetic Acid → (R)-N-[[3-(Aminocarbonylaminomethyl)phenyl]methyl]-N2-(diphenylacetyl)-argininamide acetate

HRID 1952992Notes

Reaction equation

HRID 1952992 reaction equation
[NH2:1][C:2]([NH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][NH:13][C:14](=[O:42])[C@@H:15]([CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:41])=[N:37][N+]([O-])=O)[NH:16][C:17](=[O:31])[CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:10][CH:11]=1)=[O:3].[C:43]([OH:46])(=[O:45])[CH3:44]>[Pd]>[NH2:1][C:2]([NH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][NH:13][C:14](=[O:42])[C@@H:15]([CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:37])[NH2:41])[NH:16][C:17](=[O:31])[CH:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:10][CH:11]=1)=[O:3].[C:43]([O-:46])(=[O:45])[CH3:44]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 136333684(R)N-[[3-(aminocarbonylaminomethyl)phenyl]methyl]-N5-[amino(nitroimino]methyl]-N2-(diphenylacetyl)-ornithinamide

Product 1

HCID 178476713(R)-N-[[3-(Aminocarbonylaminomethyl)phenyl]methyl]-N2-(diphenylacetyl)-argininamide acetateYield 42%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared analogously to Example 4c) from (R)N-[[3-(aminocarbonylaminomethyl)phenyl]methyl]-N5 -[amino(nitroimino]methyl]-N2 -(diphenylacetyl)-ornithinamide by catalytic hydrogenation in the presence of palladium black and 80% acetic acid in a yield of 42% of theory.

Sources & evidence

ORD record
ord-d9a78f6063ac4e1b9954f714954424a2
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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