Water → 1-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acid

HRID 1748650노트

반응식

HRID 1748650 반응식
C([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)=[O:7])(C)(C)C.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>O1CCCC1.[H-].[Na+]>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:10]2[CH:11]=[CH:12][C:8]([C:6]([OH:5])=[O:7])=[CH:9]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11171190tert-butyl 1H-pyrrole-3-carboxylate

생성물 1

HCID 27246931-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acid수율 74.2%

시약·촉매·용매 2

HCID 24758Sodium hydride촉매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60%; 1.02 mg) was added at 0° C. to a solution of 1H-pyrrole-3-carboxylic acid tert-butyl ester (3.57 g) in tetrahydrofuran (71 ml), stirred at room temperature, then p-toluenesulfonic acid chloride (4.47 g) the mixture was stirred all night and all day. Water was added to the reaction solution, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The organic solution was concentrated in vacuo, dichloromethane (30 ml) and trifluoroacetic acid (15 ml) were added to the resulting residue and stirred at room temperature for four hours. The solvent was evaporated, water was added to the resulting residue and the precipitated solid was washed with water to give 1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carboxylic acid (4.2 g) as a pale yellow solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic solution was concentrated in vacuo, dichloromethane (30 ml) and trifluoroacetic acid (15 ml)
  5. additionwere added to the resulting residue
  6. stirringstirred at room temperature for four hours
  7. customThe solvent was evaporated
  8. additionwater was added to the resulting residue
  9. washthe precipitated solid was washed with water

출처 및 근거

ORD 기록
ord-9f6fd9551b4444a4bb6b0980a041c598
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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