2-(ethoxycarbonyl)-1-tosyl-1H-indole-5-carboxylic acid → 1-(toluene-4-sulfonyl)-1H-indole-2,5-dicarboxylic acid 5-tert-butyl ester 2-ethyl ester

HRID 74456

반응식

HRID 74456 반응식
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[O:5]>C(OC(OC(C)(C)C)N(C)C)(C)(C)C.C(OCC)(=O)C.O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([O:17][C:11]([CH3:15])([CH3:12])[CH3:10])=[O:16])=[CH:10][CH:9]=2)=[O:5]

참가 물질

5

반응물 1

HCID 680048532-(ethoxycarbonyl)-1-tosyl-1H-indole-5-carboxylic acid

생성물 1

HCID 680053211-(toluene-4-sulfonyl)-1H-indole-2,5-dicarboxylic acid 5-tert-butyl ester 2-ethyl ester수율 134.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine용매2회

반응 조건

온도
80 °C

실험 절차

1-(Toluene-4-sulfonyl)-1H-indole-2,5-dicarboxylic acid 2-ethyl ester (690 mg, 1.85 mmol) was dissolved in N,N-dimethylformamide di-tert-butyl acetal (3.0 ml), and stirred at 80° C. for two and half hours. N,N-dimethylformamide di-tert-butyl acetal (2.0 ml) was further added thereto and stirred at 80° C. for three hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (150 ml) and water (75 ml). The organic layer was isolated, washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=25/1 to 5/1) to give 1-(toluene-4-sulfonyl)-1H-indole-2,5-dicarboxylic acid 5-tert-butyl ester 2-ethyl ester (551 mg, 69%).

후처리

  1. stirringstirred at 80° C. for three hours
  2. temperatureAfter cooling to room temperature
  3. customThe organic layer was isolated
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  6. customThe desiccant was removed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=25/1 to 5/1)

출처 및 근거

ORD 기록
ord-07437c96346649d795b3ab596e77bf25
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829199B2

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