O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (R)-N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[[4-[(methylamino)carbonyl]-phenyl]methyl]-ornithinamide

HRID 2393658Notes

Reaction equation

HRID 2393658 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.[CH3:31][NH:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[CH:37][CH:36]=1)=[O:34].C(C1C=CC(C(NC)=O)=CC=1)#N.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C.[Pd].CN(C)C=O>[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]([NH:42][CH2:41][C:38]1[CH:37]=[CH:36][C:35]([C:33]([NH:32][CH3:31])=[O:34])=[CH:40][CH:39]=1)=[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

Participants

8

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 50807374-Cyano-N-methylbenzamideHCID 167770714-(aminomethyl)-N-methylbenzamideHCID 136381100(R)-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithine

Product 1

HCID 136381111(R)-N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[[4-[(methylamino)carbonyl]-phenyl]methyl]-ornithinamideYield 22%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Prepared, analogously to Example 67a) but using acetonitrile as solvent instead of dimethylformamide, from (R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine, 4-[(methylamino)carbonyl]-benzenemethylamine (prepared from 4-cyano-N-methylbenzamide by catalytic hydrogenation in the presence of palladium/animal charcoal) and TBTU in a yield of 22% of theory.

Workup

  1. customPrepared, analogously to Example 67a) but

Sources & evidence

ORD record
ord-dcb7b325a3b24a929690d1827d13ef8f
Source dataset
uspto-grants-1998_09
Patent number
US05807875

Reaction notes

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