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

HRID 1648288

Reaktionsgleichung

Reaktionsgleichung von HRID 1648288
[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][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:27]=2[CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:37][C:35]([CH3:38])([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])[CH3:36]

Komponenten

5

Edukt 3

HCID 82127Potassium hydrideHCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylateHCID 15744966Diethyl (dipropylamino)propanedioate

Produkt 1

HCID 15744967diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioateAusbeute 80,7 %

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}(dipropyl amino)-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-02c10acca5c44d4182e4e0f418745082
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436240

Verknüpfte Notizen

Wird geladen…