Potassium Carbonate → 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester

HRID 1643221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643221
[CH2:1]([N:5]1[C:9]([CH2:10][NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:7]=[C:6]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:2][CH2:3][CH3:4].[O:33]([C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:40]Br)[C:34]([CH3:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:48]([O:47][C:45](=[O:46])[C:44]1[CH:43]=[CH:42][C:39]([CH2:40][N:11]([CH2:10][C:9]2[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][C:8]=2[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:38][C:37]=1[O:33][C:34](=[O:35])[CH3:36])([CH3:51])([CH3:50])[CH3:49]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 184378533-Acetoxyl-4-tert-butoxycarbonyl-benzyl bromideHCID 58818024[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

Produkt 1

HCID 588179794-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl esterAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine (4.0 g, 9.31 mmol) and 3-acetoxyl-4-tert-butoxycarbonyl-benzyl bromide (3.37 g, 10.24 mmol, 1.1 eq.) in 50 ml anhydrous acetonitrile is added anhydrous potassium carbonate (2.82 g, 20.5 mmol, 2.2 eq.), the resulting mixture is stirred at room temperature for 1 h, then raised to 50° C., stirred overnight. The solid precipitate is filtered off, washed with ethyl acetate, the combined organics is concentrated to dryness, purified through silica gel flash chromatography to give 3.99 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester MS (+VE) m/z 680 (M+1).

Aufarbeitung

  1. temperatureraised to 50° C.
  2. stirringstirred overnight
  3. filtrationThe solid precipitate is filtered off
  4. washwashed with ethyl acetate
  5. concentrationthe combined organics is concentrated to dryness
  6. custompurified through silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7b025043345248e5b2404c0d43cf4a37
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119665B2

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