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Sodium Hydroxide → 7-[2-Methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid

HRID 1188913
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인쇄 미리보기

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HRID 1188913 반응식
[CH3:1][O:2][CH2:3][CH:4]([CH2:30][O:31][CH3:32])[O:5][C:6]1[CH:7]=[C:8]([O:19][C:20]2[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11]2.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][O:2][CH2:3][CH:4]([CH2:30][O:31][CH3:32])[O:5][C:6]1[CH:7]=[C:8]([O:19][C:20]2[CH:21]=[N:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]2
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5

반응물 2

HCID 14798Sodium HydroxideHCID 66897495Methyl 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate

생성물 1

HCID 668979397-[2-Methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid수율 69%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

To a solution of methyl 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.79 g) in a mixture of tetrahydrofuran (20 mL) and methanol (15 mL) was added 1M aqueous sodium hydroxide solution (15 mL), and the mixture was stirred at 50° C. for 30 min. The mixture was concentrated under reduced pressure and the residue was dissolved in water. The mixture was washed with diethyl ether three times. The diethyl ether layers were combined and extracted with water. The aqueous layers were combined and 1M hydrochloric acid (15 mL) was added to the mixture. The resulting white suspension was filtered to give the title compound (1.02 g, 69%) as a pale orange solid. MS 451 (MH+).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washThe mixture was washed with diethyl ether three times
  4. extractionextracted with water
  5. addition1M hydrochloric acid (15 mL) was added to the mixture
  6. filtrationThe resulting white suspension was filtered

출처 및 근거

ORD 기록
ord-dd3975aca8fe4d59a442136936565865
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673942B2

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