Reacción #93655

ord-03917697abbc44dd951a07c2fa6fb6e5

Ecuación de reacción

C(=NC1CCCCC1)=NC1CCCCC1
DCCI
N=C(N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)O
Z-Phe-Arg-OH
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](Cc1c[nH]cn1)C(N)=O
H-Leu-Val-Ile-His-NH2
On1nnc2ccccc21
HOBt
→
CC[C@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(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](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(N)=O
Z-Phe-Arg-Leu-Val-Ile-His-NH2

Reactantes

C(=NC1CCCCC1)=NC1CCCCC1
DCCI
N=C(N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)O
Z-Phe-Arg-OH
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](Cc1c[nH]cn1)C(N)=O
H-Leu-Val-Ile-His-NH2
On1nnc2ccccc21
HOBt

Reactivos

Ninguno

Disolventes

CO.ClCCl.O
methylene chloride methanol water

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 69 mg of Z-Phe-Arg-OH, 50 mg of H-Leu-Val-Ile-His-NH2, 16 mg of HOBt and 40 mg of DCCI, the title compound is obtained in the form of a colourless powder after flash chromatography (45 g of silica gel 60, 40-63 μm, eluant system methylene chloride/methanol/water/glacial acetic acid 330:100: 19:2). Rf (S3)=0.16.

Fuente

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