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Sodium Hydroxide → HCID 57772003, 화합물

HRID 1661922
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HRID 1661922 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:35][CH3:36])=[CH:20][C:21]([CH:23](OS(C)(=O)=O)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:35][CH3:36])=[CH:20][C:21]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:22][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57772049methanesulfonic acid [2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-pyridin-2-yl-methyl ester

생성물 1

HCID 57772003HCID 57772003, 화합물수율 19.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ca. 250 mg of methanesulfonic acid [2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-pyridin-2-yl-methyl ester in 7 ml THF, 50 mg LiAlH4 are added. The mixture is heated to reflux temperature and stirred for 3 h. After that the reaction mixture is allowed to cool to room temperature and 1N NaOH solution is added and this mixture is stirred for 30 min and filtered. The filtrate is extracted with ethyl acetate (3×). The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (CH2Cl2:MeOH=95:5) to afford 40 mg of the title compound as an oil.

후처리

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. stirringthis mixture is stirred for 30 min
  4. filtrationfiltered
  5. extractionThe filtrate is extracted with ethyl acetate (3×)
  6. washThe combined organic layers are washed with water (2×) and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is purified by flash-chromatography on silica gel (CH2Cl2:MeOH=95:5)

출처 및 근거

ORD 기록
ord-d5a8fe5c57bd4199818b2c9d9d14b063
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030497B2

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