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 1188889ノート

反応式

HRID 1188889 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒3 回

反応条件

温度
50 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-6f8a42cbab71404d8c80fad9c6ee8c4c
出典データセット
uspto-grants-2014_03
特許番号
US08673942B2

反応ノート

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