Reacción #93651

ord-90cb005c02aa4302a22499ad366c6512

Ecuación de reacción

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@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CC(C)C)C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(N)=O
H-Leu-Val-Ile-Sta-NH2
→
CC[C@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(N)=O
title compound
CC[C@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(N)=O
Z-Phe-His-Leu-Val-Ile-Sta-NH2

Reactantes

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@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CC(C)C)C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(N)=O
H-Leu-Val-Ile-Sta-NH2

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

In a manner analogous to that described in Example 1, using as starting materials 125 mg of Z-Phe-His-OH, 110 mg of H-Leu-Val-Ile-Sta-NH2, 44 mg of HOBt and 68 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)=0.20, Rf (B11)=0.64.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04613676uspto-grants-1986_09