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Nitrogen → HCID 57719158, Verbindung

HRID 1985241
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1985241
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[CH3:18][C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[CH2:28][CH:27]([CH2:29][CH2:30]OS(C3C=CC(C)=CC=3)(=O)=O)[N:26]([CH2:42][CH2:43][CH3:44])[C:25]2=[O:45])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].N#N.[OH-].[Na+]>C(O)C>[CH3:18][C:19]1[CH:47]=[CH:46][C:22]([CH2:23][N:24]2[CH2:28][CH:27]([CH2:29][CH2:30][O:17][C:14]3[CH:13]=[CH:12][C:11]([C:6]4([C:4]([OH:3])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10]4)=[CH:16][CH:15]=3)[N:26]([CH2:42][CH2:43][CH3:44])[C:25]2=[O:45])=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57718928HCID 57718928, VerbindungHCID 57719317HCID 57719317, Verbindung

Produkt 1

HCID 57719158HCID 57719158, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-hydroxy-phenyl)-cyclopentanecarboxylic acid ethyl ester (0.042 g, 0.179 mmol), toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethyl ester (0.085 g, 0.197 mmol) and 325 mesh K2CO3 (0.050 g, 0.362 mmol) in ethanol (5 mL) was heated at ref lux for under N2 for 16 h. The reaction was then treated with aqueous 5 N NaOH (0.5 mL) and heated to reflux 1.5 h. The reaction mixture was cooled, the solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (10 mL) and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 0.058 g crude acid that was purified by preparative HPLC to afford 0.033 g (40%) 1-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-cyclopentanecarboxylic acid. MS (ES+) Calc'd for C28H37N2O4 (M+1) 465. Found m/z 465 (100%). 1H NMR.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed in vacuo
  5. extractionextracted with Et2O
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto afford 0.058 g crude acid that
  9. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-47e13ea165ca4f45ae068b65d00b2349
Quelldatensatz
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07544812B2

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