Reaktion #80876

ord-e7044d2e21e443a88af663f3fb94999d

Reaktionsgleichung

CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CCOc1ccc(C#N)cc1
4-ethoxybenzonitrile
Cl
hydrochloric acid
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
ester-C
CC(C)(C)OC(=O)N[C@H](CCCN=C(N)N[N+](=O)[O-])C(=O)O
Boc-D-Arg-(NO2)-OH
CCOc1ccc(CN)cc1.Cl
4-ethoxybenzenemethylamine-hydrochloride
→
CCOc1ccc(CNC(=O)[C@@H](CCCNC(N)=N[N+](=O)[O-])NC(=O)OC(C)(C)C)cc1
(R)-N5 -[Amino(nitroimino)methyl]-N2 -[(tert.-butyloxy)-carbonyl]-N-[(4-ethoxyphenyl)methyl]-ornithinamide
Ausbeute 77.0%

Edukte

CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CCOc1ccc(C#N)cc1
4-ethoxybenzonitrile
Cl
hydrochloric acid
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
ester-C
CC(C)(C)OC(=O)N[C@H](CCCN=C(N)N[N+](=O)[O-])C(=O)O
Boc-D-Arg-(NO2)-OH
CCOc1ccc(CN)cc1.Cl
4-ethoxybenzenemethylamine-hydrochloride
—
amide
—
amide

Reagenzien

[Pd]
palladium

Lösungsmittel

CCN(CC)CC
triethylamine
ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared analogously to Example 8a) from Boc-D-Arg-(NO2)-OH, 4-ethoxybenzenemethylamine-hydrochloride (mp.: 262°-264° C.; from 4-ethoxybenzonitrile by catalytic hydrogenation in the presence of palladium/animal charcoal and aqueous hydrochloric acid), triethylamine and TBTU in a yield of 77% of theory. IR (CH2Cl2): 1730 cm-1 (ester-C=O) 1675 cm-1 (amide C=O) 1510 cm-1 (amide II)

Quelle

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