O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (R)-N-[[4-[2-(Aminocarbonyl)ethyl]phenyl]methyl]-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithinamide

HRID 1953011Notes

Reaction equation

HRID 1953011 reaction equation
[NH2:1][C:2](=[N:27][N+:28]([O-:30])=[O:29])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:24](O)=[O:25])[NH:8][C:9](=[O:23])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:31][C:32]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH2:43])=[CH:38][CH:37]=1)=[O:33].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[NH2:31][C:32]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH:43][C:24](=[O:25])[C@@H:7]([CH2:6][CH2:5][CH2:4][NH:3][C:2]([NH2:1])=[N:27][N+:28]([O-:30])=[O:29])[NH:8][C:9](=[O:23])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:38][CH:37]=1)=[O:33]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 23301859HCID 23301859, compoundHCID 136381100(R)-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithine

Product 1

HCID 136333691(R)-N-[[4-[2-(Aminocarbonyl)ethyl]phenyl]methyl]-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithinamideYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared analogously to Example 4b) from (R)-N5 -[amino[nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine, 4-[2-(aminocarbonyl)ethyl]benzenemethanamine and TBTU in a yield of 60% of theory. Colourless crystals, Mp. 139-140° C. (Acetonitrile).

Sources & evidence

ORD record
ord-0688dc68c3ef4a69ad0f2bce642d6fa6
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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