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Triethylamine → 4-methoxycarbonyl-4-methyl-pentanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide

HRID 2380677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2380677
[CH3:1][O:2][C:3]([C:5]([CH3:12])([CH3:11])[CH2:6][CH2:7][C:8](Cl)=[O:9])=[O:4].[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=1)#[N:14].C(N(CC)CC)C>C(Cl)Cl>[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[CH:23][C:24]([CH2:27][N:28]([CH2:29][CH2:30][CH3:31])[C:8](=[O:9])[CH2:7][CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:12])[CH3:11])=[CH:25][CH:26]=1)#[N:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 14980523Methyl 5-chloro-2,2-dimethyl-5-oxopentanoateHCID 15338355N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine

Produkt 1

HCID 538386644-methoxycarbonyl-4-methyl-pentanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

The starting material can be prepared, for example, as follows: 2.89 g of 4-methoxycarbonyl-4-methyl-pentanoic acid chloride are added to a solution of 2.50 g of N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amine and 2.09 ml of triethylamine in 100 ml of CH2Cl2, and the mixture is stirred for 1 hour. The reaction mixture is washed twice with 50 ml of water each time and the combined aqueous phases are extracted with 50 ml of CH2Cl2. The crude product obtained from the organic phase by the customary procedure is purified by chromatography on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (98:2) as eluant to yield pure 4-methoxycarbonyl-4-methyl-pentanoic acid N-(2'-cyanobiphenyl-4-ylmethyl)-N-propyl-amide that has an Rf value of 0.56 [CH2Cl2 /CH3OH (95:5)].

Aufarbeitung

  1. washThe reaction mixture is washed twice with 50 ml of water each time
  2. extractionthe combined aqueous phases are extracted with 50 ml of CH2Cl2
  3. customThe crude product obtained from the organic phase by the customary procedure
  4. customis purified by chromatography on silica gel 60 (40-63 μm)

Quellen und Nachweise

ORD-Eintrag
ord-91587b9ce4e6426a87ba72a1d3d4abf9
Quelldatensatz
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05369110

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