HCID 13772485, Verbindung → HCID 13772487, Verbindung

HRID 986315

Reaktionsgleichung

Reaktionsgleichung von HRID 986315
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([NH:19][CH2:20][CH:21]([OH:50])[CH2:22][NH:23][C:24](=[O:49])[C@H:25]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[NH:26]C(OCC1C=CC=CC=1)=O)=[O:18].[H][H]>COCCOC.CN(C)C=O.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([NH:19][CH2:20][CH:21]([OH:50])[CH2:22][NH:23][C:24](=[O:49])[C@H:25]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[NH2:26])=[O:18]

Komponenten

5

Edukt 2

HCID 13772485HCID 13772485, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 13772487HCID 13772487, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 18463208dimethoxyethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

1.80 g (2.46 mmol) of Nα -benzyloxycarbonyl-Nε -tert.-butoxycarbonyl-L-lysine-3-{2-[2-(2,6-dichlorophenylamino)-phenyl]-acetylamino}-2-hydroxypropylamide are dissolved in 100 ml of 1,2-dimethoxyethane/dimethylformamide (9:1) and after the addition of 0.40 g of palladium-on-carbon (10%) the whole is treated for 11/4 hours with hydrogen. The catalyst is filtered off, the filtrate is concentrated by evaporation at 30° in a rotary evaporator and the residue is lyophilised after being taken up in 100 ml of dioxan/water (7:3). Nε -tert.-butoxycarbonyl-L-lysine-3-{2-[2-(2,6-dichlorophenylamino)-phenyl]-acetylamino}-2hydroxypropylamide is obtained in the form of a colourless powder which is immediately processed further; Rf =0.52 (acetonitrile:water=3:1), Rf =0.66 (ethyl acetate:n-butanol:pyridine:acetic acid:water=42:21:21:6:10).

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated by evaporation at 30° in a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-87e05433a8e54a0186dcfb21f9f5cae6
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04711879

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