Nitrogen → HCID 68867376, Verbindung

HRID 1985220

Reaktionsgleichung

Reaktionsgleichung von HRID 1985220
[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:46])[C:35]([O:38][C:39]1[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=1)([CH3:37])[CH3:36])[CH3:32].N#N>CN(C=O)C>[CH2:31]([O:33][C:34](=[O:46])[C:35]([CH3:37])([O:38][C:39]1[CH:44]=[CH:43][C:42]([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:41][CH:40]=1)[CH3:36])[CH3:32]

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateHCID 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 68867376HCID 68867376, VerbindungAusbeute 19,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

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 (0.194 g, 1.51 mmol), 2-(4-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester (0.088 g, 0.392 mmol) and CS2CO3 (0.156 g, 0.478 mmol) in DMF (15 mL) was heated at 55° C. for under N2 for 16 h. The reaction mixture was cooled to room temperature, quenched with aqueous 1 N HCl (2 mL), and worked up extractively with EtOAc and water. 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 1:1 hexanes:acetone to afford 0.036 g (19%) 2-methyl-2-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester.

Aufarbeitung

  1. customquenched with aqueous 1 N HCl (2 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto afford crude product that
  5. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-58b0f8cdf85949cebbf68281547aa1b9
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544812B2

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