Potassium Carbonate → tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

HRID 1698570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698570
[CH2:1]([CH:3]([C:6]1[C:14]2[NH:13][C:12](=[O:15])[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32]>CN(C)C=O.O>[CH2:1]([CH:3]([C:6]1[C:14]2[N:13]([CH2:30][C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[C:12](=[O:15])[N:11]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 67272646tert-Butyl 4-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

Produkt 1

HCID 67273576tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylateAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of tert-butyl 4-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (7.70 g, 25.3 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (3.84 g, 27.8 mmol) and isopropyl bromoacetate (3.60 ml, 27.8 mmol), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (X2). The combined organic layer was washed with aqueous sodium chloride (X2) and brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column, chromatography eluting with a 5-20% ethyl acetate/hexane gradient mixture to give 8.95 g (22.1 mmol, 87.5%) of the title compound as a colorless oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate (X2)
  2. washThe combined organic layer was washed with aqueous sodium chloride (X2) and brine (X1)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column, chromatography
  6. washeluting with a 5-20% ethyl acetate/hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-2212780be9b04c6eab5b99d1fe4b765f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163935B2

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