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

HRID 1698570노트

반응식

HRID 1698570 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 67273576tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate수율 87.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2212780be9b04c6eab5b99d1fe4b765f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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