Reaktion #80870

ord-643370c841a84dca854cc1e371cf6247

Reaktionsgleichung

NC(=N[N+](=O)[O-])NCCC[C@@H](NC(=O)C(c1ccccc1)c1ccccc1)C(=O)O
(R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine
CNC(=O)c1ccc(CN)cc1
4-[(methylamino)carbonyl]benzenemethylamine
CNC(=O)c1ccc(C#N)cc1
4-cyano-N-methylbenzamide
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
→
CNC(=O)c1ccc(CNC(=O)[C@@H](CCCNC(N)=N[N+](=O)[O-])NC(=O)C(c2ccccc2)c2ccccc2)cc1
(R)-N5 -[Amino(nitroimino)methyl]-N2 -(diphenylacetyl)-N-[[4-[(methylamino)carbonyl]phenyl]methyl]-ornithinamide
Ausbeute 22.0%

Edukte

NC(=N[N+](=O)[O-])NCCC[C@@H](NC(=O)C(c1ccccc1)c1ccccc1)C(=O)O
(R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine
CNC(=O)c1ccc(CN)cc1
4-[(methylamino)carbonyl]benzenemethylamine
CNC(=O)c1ccc(C#N)cc1
4-cyano-N-methylbenzamide
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU

Reagenzien

[Pd]
palladium

Lösungsmittel

CN(C)C=O
dimethylformamide
CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared, analogously to Example 67a) but

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05616620uspto-grants-1997_04