Réaction #80868

ord-1c1598767bea497387d3419ad8b568de

Équation de réaction

CC(C)(C)OC(=O)N[C@@H](CCCNC(=N)N[N+](=O)[O-])C(=O)O
Boc-Arg(NO2)-OH
NCc1cccs1
thiophene-2-methanamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CC(C)(C)OC(=O)N[C@H](CCCNC(N)=N[N+](=O)[O-])C(=O)NCc1cccs1
(R)-N5 -[amino(nitroimino)methyl]-N2 -[(tert.-butyloxy)carbonyl]-N-[(2-thienyl)methyl]-ornithinamide
O=C(O)C(F)(F)F
trifluoroacetic acid
→
NC(=N[N+](=O)[O-])NCCC[C@@H](N)C(=O)NCc1cccs1
crude product
NC(=N[N+](=O)[O-])NCCC[C@@H](N)C(=O)NCc1cccs1
(R)-N5 -[Amino(nitroimino)methyl]-N-[(2-thienyl)methyl]-ornithinamide

Réactifs

CC(C)(C)OC(=O)N[C@@H](CCCNC(=N)N[N+](=O)[O-])C(=O)O
Boc-Arg(NO2)-OH
NCc1cccs1
thiophene-2-methanamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CC(C)(C)OC(=O)N[C@H](CCCNC(N)=N[N+](=O)[O-])C(=O)NCc1cccs1
(R)-N5 -[amino(nitroimino)methyl]-N2 -[(tert.-butyloxy)carbonyl]-N-[(2-thienyl)methyl]-ornithinamide
O=C(O)C(F)(F)F
trifluoroacetic acid

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

First of all Boc-Arg(NO2)-OH was reacted with thiophene-2-methanamine and TBTU as in Example 8a). The resulting (R)-N5 -[amino(nitroimino)methyl]-N2 -[(tert.-butyloxy)carbonyl]-N-[(2-thienyl)methyl]-ornithinamide was then reacted, without purification, with trifluoroacetic acid as in Example 23b). The crude product obtained in a quantitative yield was further processed without purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05616620uspto-grants-1997_04