Potassium hydride → diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioate

HRID 327445

Reaktionsgleichung

Reaktionsgleichung von HRID 327445
[H-].[K+].[CH2:3]([N:6]([CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH3:9])[CH2:4][CH3:5].Br[CH2:22][C:23]1[C:31]2[N:30]=[CH:29][N:28]([C:32]([O-:34])=[O:33])[C:27]=2[CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:22][C:23]([CH3:31])([O:34][C:32]([N:28]1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:22][C:10]([N:6]([CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH3:5])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:31]=2[N:30]=[CH:29]1)=[O:33])[CH3:24]

Komponenten

5

Edukt 3

HCID 82127Potassium hydrideHCID 15744966Diethyl (dipropylamino)propanedioateHCID 19108494HCID 19108494, Verbindung

Produkt 1

HCID 15744967diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioateAusbeute 161,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium hydride (3.3 g of 40% oil suspension, washed with ether to remove oil, 0.03 mol) was added to a stirred solution of diethyl (dipropylamino)-malonate (10.2 g, 0.039 mol) in dry THF (100 mL). After 5 minutes, t-butyl, 4-(bromomethyl)-1H-benzimidazole-1-carboxylate (6.22 g, 0.02 mol) was added and the solution was refluxed for 6 hours. The solvent was removed under reduced pressure and the residual oil was partitioned between ethyl acetate and water. After evaporation of the ethyl acetate, the crude product was chromatographed on silica gel using ethyl acetate:hexane as the eluant to give 7.9 g of diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioate as an oil.

Aufarbeitung

  1. temperaturethe solution was refluxed for 6 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residual oil was partitioned between ethyl acetate and water
  4. customAfter evaporation of the ethyl acetate
  5. customthe crude product was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7a3d32195c9948809b36a92171542aa8
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273975

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