Reaktion #93638

ord-8b69f0843db34615a3ce494cbb020f11

Reaktionsgleichung

On1nnc2ccccc21
HOBt
O=C(N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)O)OCc1ccccc1
Z-Phe-His-OH
C(=NC1CCCCC1)=NC1CCCCC1
DCCI
CC(C)C[C@H](N)C(=O)N[C@H](C(=O)O)C(C)C.[NH-]CC(O)COc1cccc(C(N)=O)c1
H-Leu-Val 3-(m-carbamoylphenoxy)- 2-hydroxypropyl amide
→
CC(C)C[C@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)N[C@H](C(=O)O)C(C)C.[NH-]CC(O)COc1cccc(C(N)=O)c1
title compound
CC(C)C[C@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)N[C@H](C(=O)O)C(C)C.[NH-]CC(O)COc1cccc(C(N)=O)c1
Z-Phe-His-Leu-Val 3-(m-carbamoylphenoxy)-2-hydroxypropyl amide

Edukte

On1nnc2ccccc21
HOBt
O=C(N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)O)OCc1ccccc1
Z-Phe-His-OH
C(=NC1CCCCC1)=NC1CCCCC1
DCCI
CC(C)C[C@H](N)C(=O)N[C@H](C(=O)O)C(C)C.[NH-]CC(O)COc1cccc(C(N)=O)c1
H-Leu-Val 3-(m-carbamoylphenoxy)- 2-hydroxypropyl amide

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

In a manner analogous to that described in Example 1, using as starting materials 77 mg of Z-Phe-His-OH, 37 mg of H-Leu-Val-3-(m-carbamoylphenoxy)- 2-hydroxypropyl amide, 27 mg of HOBt and 36 mg of DCCI, the title compound is obtained after flash chromatography (65 g of silica gel 60, 40-63 μm, eluant system B7). Rf (B7)=0.15, Rf (N12)=0.30.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04613676uspto-grants-1986_09