Reaktion #93629

ord-1787760d09d44c54a8141bf8966e1713

Reaktionsgleichung

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.C[SiH](C)OC(C(C)(C)C)C(NC(=O)CCCC[NH-])(C(O[SiH](C)C)C(C)(C)C)C(O[SiH](C)C)C(C)(C)C
Z-Phe-His-Leu-Val 4-[-tris-(tert.-butyldimethylsilyloxymethyl)-methylaminocarbonyl]-butyl 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-]CCCCC(=O)NC(CO)(CO)CO
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-]CCCCC(=O)NC(CO)(CO)CO
Z-Phe-His-Leu-Val 4-[tris-(hydroxymethyl)-methylaminocarbonyl]-butyl amide

Edukte

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.C[SiH](C)OC(C(C)(C)C)C(NC(=O)CCCC[NH-])(C(O[SiH](C)C)C(C)(C)C)C(O[SiH](C)C)C(C)(C)C
Z-Phe-His-Leu-Val 4-[-tris-(tert.-butyldimethylsilyloxymethyl)-methylaminocarbonyl]-butyl amide

Reagenzien

Keine

Lösungsmittel

CC(=O)O.O
acetic acid water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter evaporating off the solvent and medium-pressure chromatography (60 g of Lichroprep® Si60, 40-60 μm, system B8)

Vorschrift

83 mg of Z-Phe-His-Leu-Val-4-[-tris-(tert.-butyldimethylsilyloxymethyl)-methylaminocarbonyl]-butyl amide (Example 19) are stirred at room temperature for 2 hours with 6 ml of glacial acetic acid/water 2:1. After evaporating off the solvent and medium-pressure chromatography (60 g of Lichroprep® Si60, 40-60 μm, system B8), the title compound is obtained in the form of a colourless powder. Rf (methylene chloride/methanol/concentrated ammonia 70:10:1)=0.11.

Quelle

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