Cesium carbonate → HCID 68866819, Verbindung

HRID 1985224

Reaktionsgleichung

Reaktionsgleichung von HRID 1985224
[CH3:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([CH2:12][CH2:13][O:14]S(C3C=CC(C)=CC=3)(=O)=O)[N:9]([CH2:25][CH2:26][CH3:27])[C:8]2=[O:28])=[CH:4][CH:3]=1.[CH2:31]([O:33][C:34](=[O:52])[C:35]([CH3:51])([O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:36][C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1)[CH3:32].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:31]([O:33][C:34](=[O:52])[C:35]([CH3:51])([O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:14][CH2:13][CH2:12][C:10]2[N:9]([CH2:25][CH2:26][CH3:27])[C:8](=[O:28])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:30][CH:29]=3)[CH:11]=2)=[CH:39][CH:38]=1)[CH3:32]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 57719269toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethyl ester

Produkt 1

HCID 68866819HCID 68866819, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethyl ester (0.029 g, 0.0677 mmol), 3-(4-Hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.018 g, 0.0599 mmol) and Cs2CO3 (0.024 g, 0.0736 mmol) in DMF (3 mL) was heated at 55° C. under N2 for 16 h. The reaction mixture was cooled to room temperature and quenched with aqueous 1 N HCl (0.3 mL) and then was diluted with water and extracted with Et2O. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using a gradient of 4:1 to hexanes:EtOAc to 2:1 EtOAc:hexanes to afford 0.011 g (32%) 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with aqueous 1 N HCl (0.3 mL)
  3. additionwas diluted with water
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto afford crude product that
  8. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bc71db463942437ab8f7966f01b8081d
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544812B2

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