Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate → 7-(2-{[Di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid

HRID 1188889노트

반응식

HRID 1188889 반응식
[C:1]([Si:5]([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[O:6][CH2:7][CH:8]([CH3:35])[O:9][C:10]1[CH:11]=[C:12]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15]2)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.C(O)C.[OH-].[Na+]>[C:42]([Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[O:6][CH2:7][CH:8]([CH3:35])[O:9][C:10]1[CH:11]=[C:12]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15]2)([CH3:45])([CH3:43])[CH3:44]

참가 물질

5

반응물 1

HCID 67118494Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

생성물 1

HCID 668982647-(2-{[Di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid수율 83%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매3회

반응 조건

온도
50 °C

실험 절차

Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (2.4 g) was dissolved in a mixed solvent of tetrahydrofuran (10 mL)-ethanol (10 mL), 1M aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at 50° C. for 1 hr. 1M Aqueous sodium hydroxide solution (1 mL) was added to the reaction solution, and the mixture was stirred at 50° C. for 40 min. 1M Aqueous sodium hydroxide solution (1 mL) was added again, and the mixture was further stirred at 50° C. for 30 min. 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, filtrated, and concentrated under reduced pressure to give the title compound (1.9 g, yield 83%) as a pale-red amorphous solid. MS 644 (MH+).

후처리

  1. additionwas added
  2. stirringthe mixture was stirred at 50° C. for 40 min
  3. stirringthe mixture was further stirred at 50° C. for 30 min
  4. temperatureto cool to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionsubjected to extraction with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6f8a42cbab71404d8c80fad9c6ee8c4c
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673942B2

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