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Sodium hydride → tert-Butyl 3-(1-tert-butoxycarbonyl-2-phenylethyl)-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

HRID 1631967
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HRID 1631967 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH:22]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:26]([O:25][C:23]([CH:22]([N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=2[N:6]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C:7]1=[O:9])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:24])([CH3:29])([CH3:27])[CH3:28]
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참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10468275tert-Butyl 5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylateHCID 12158486tert-Butyl 2-bromo-3-phenylpropionate

생성물 1

HCID 24901094tert-Butyl 3-(1-tert-butoxycarbonyl-2-phenylethyl)-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

1.20 g (4.47 mmol) of tert-butyl 5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (VIa) were dissolved in dry DMF (15 ml) in a heat-dried flask under a nitrogen atmosphere. 187 mg (4.69 mmol) of sodium hydride (60% suspension in mineral oil) were added while stirring at 0° C., and the reaction solution was then stirred at room temperature for 30 min. After renewed cooling in an ice bath, 1.40 g (4.91 mmol) of tert-butyl 2-bromo-3-phenylpropionate were added, and the mixture was stirred while cooling in ice for 1 h and then at room temperature for 2 h. The reaction solution was diluted with ethyl acetate, mixed with 10% aqueous ammonium chloride solution and then extracted with ethyl acetate (3×). The combined organic phases were washed with water and saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 15-30% ethyl acetate in heptane). Yield: 1.3 g (62%) of colorless oil

후처리

  1. stirringthe reaction solution was then stirred at room temperature for 30 min
  2. temperatureAfter renewed cooling in an ice bath
  3. stirringthe mixture was stirred
  4. temperaturewhile cooling in ice for 1 h
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined organic phases were washed with water and saturated NaCl solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (mobile phase gradient 15-30% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-165629a2ada5405284486be1d6ad5b94
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08791148B2

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