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

HRID 327445노트

반응식

HRID 327445 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 15744967diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioate수율 161.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7a3d32195c9948809b36a92171542aa8
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273975

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