Réaction #93639

ord-3e9e24a873b84efbb35500784024abbb

Équation de réaction

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-]CCCN1CCCC1=O
H-Leu-Val 3-(2-pyrrolidinon-1-yl)-propyl 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-]CCCN1CCCC1=O
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-]CCCN1CCCC1=O
Z-Phe-His-Leu-Val 3-(2-pyrrolidinon-1-yl)-propyl amide

Réactifs

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-]CCCN1CCCC1=O
H-Leu-Val 3-(2-pyrrolidinon-1-yl)-propyl amide

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

In a manner analogous to that described in Example 1, using as starting materials 221 mg of Z-Phe-His-OH, 150 mg of H-Leu-Val-3-(2-pyrrolidinon-1-yl)-propyl amide, 77 mg of HOBt and 122 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)=0.26, Rf (N12)=0.34.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04613676uspto-grants-1986_09