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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → 1-(4-methoxybutyl)-1H-indole-2-carboxylic acid

HRID 1259881
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HRID 1259881 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]C)=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])(=O)=O>CC(N(C)C)=O>[CH3:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 70992Methyl 1H-indole-2-carboxylateHCID 116870064-Methoxybutyl methanesulfonate

생성물 1

HCID 583555091-(4-methoxybutyl)-1H-indole-2-carboxylic acid수율 81.4%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
60 °C

실험 절차

Methyl 1H-indole-2-carboxylate (0.67 g), cesium carbonate (1.9 g) and 4-methoxybutyl methanesulfonate (0.70 g) were suspended in DMA (20 ml), and the suspension was stirred at 60° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (0:10-4:6) was concentrated under reduced pressure. The obtained residue was dissolved in methanol (10 ml), 4N aqueous sodium hydroxide solution (5 ml) was added, and the mixture was heated at 80° C. for 2 hr. The mixture was allowed to cool to room temperature, acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the object product (0.77 g).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washa fraction eluted with ethyl acetate-hexane (0:10-4:6)
  8. concentrationwas concentrated under reduced pressure
  9. dissolutionThe obtained residue was dissolved in methanol (10 ml)
  10. addition4N aqueous sodium hydroxide solution (5 ml) was added
  11. temperaturethe mixture was heated at 80° C. for 2 hr
  12. temperatureto cool to room temperature
  13. extractionextracted with ethyl acetate
  14. washThe extract was washed with saturated brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f031be08e8ed442f8407100fcbf73b3a
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466282B2

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