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Dicyclohexylcarbodiimide → Ethyl 4-(2-(11-Bromoundecanoylamino)phenoxy)-butyrate

HRID 1003246
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1003246
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 1781211-Bromoundecanoic acidHCID 11816929Ethyl 4-(2-aminophenoxy)butanoate

Produkt 1

HCID 19603128Ethyl 4-(2-(11-Bromoundecanoylamino)phenoxy)-butyrateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of (4) (2.60 g., 11 mM) and 11-bromoundecanoic acid (2.65 g., 10 mM) in anhydrous methylene chloride (90 mL) is added 4-(dimethylamino)pyridine (1.22 g., 10 mM) followed by N,N'-dicyclohexylcarbodiimide (2.3 g., 11 mM) (4×5 mL of methylenechloride rinses). Precipitation of dicyclohexylurea (DCU) begins within 4 minutes. When TLC analysis indicates the reaction is complete, the mixture is filtered, the filtrate concentrated in vacuo and the residue extracted with ether. The combined ether extracts are washed 1× with 1N hydrochloric acid, 1× saturated sodium chloride solution, dried (Na2SO4) and concentrated to a residue which is stirred, filtered, and concentrated alternately with ether and methylene chloride until all DCU is removed. Concentration of the final solution yields the title product (32) (2.35 g.) as an oil that goes readily to a waxy solid.

Aufarbeitung

  1. customPrecipitation of dicyclohexylurea (DCU)
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. extractionthe residue extracted with ether
  5. washThe combined ether extracts are washed 1× with 1N hydrochloric acid, 1× saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to a residue which
  8. filtrationfiltered
  9. concentrationconcentrated alternately with ether and methylene chloride until all DCU
  10. customis removed

Quellen und Nachweise

ORD-Eintrag
ord-4504c21258284ba5a6ca88c44d58873d
Quelldatensatz
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06046183

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