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Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate → 5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylic acid

HRID 1188885
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HRID 1188885 반응식
[CH3:1][S:2]([C:5]1[CH:33]=[CH:32][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:18]=2)[NH:15][C:14]([C:27]([O:29]CC)=[O:28])=[CH:13]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>O1CCCC1.C(O)C.[OH-].[Na+]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:18]=2)[NH:15][C:14]([C:27]([OH:29])=[O:28])=[CH:13]3)=[CH:32][CH:33]=1)(=[O:3])=[O:4]
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참가 물질

5

반응물 1

HCID 66898356Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate

생성물 1

HCID 668978135-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylic acid수율 33.4%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide
용매

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온도
50 °C

실험 절차

Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate (3.5 g) was dissolved in a mixed solvent of tetrahydrofuran (30 mL)-ethanol (30 mL), 1M aqueous sodium hydroxide solution (15 mL) was added, and the mixture was stirred at 50° C. for 1 hr. The reaction solution was allowed to cool to room temperature, and concentrated under reduced pressure. Water was added to the residue, and the mixture was neutralized with 1M hydrochloric acid, and subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was crystallized from a mixed solvent of ethanol-hexane-diethyl ether. The obtained colorless crystals were recrystallized from acetone-hexane to give the title compound (1.1 g) as colorless crystals. melting point 256-258° C. (decomposition).

후처리

  1. additionwas added
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionsubjected to extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas crystallized from a mixed solvent of ethanol-hexane-diethyl ether
  12. customThe obtained colorless crystals were recrystallized from acetone-hexane

출처 및 근거

ORD 기록
ord-ee20c4cbabf942a2bb9b31cf19e34e06
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673942B2

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