Tetrahydrofuran → 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylic acid

HRID 2068879노트

반응식

HRID 2068879 반응식
[CH3:1][C:2]1([CH3:40])[CH2:10][C:9]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[C:6]([C:19]3[N:20]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([C:28]([O:30]C)=[O:29])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1.O1CCCC1.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:40])[CH2:10][C:9]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[N:7]=[C:6]([C:19]3[N:20]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:39])[CH3:38])[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([C:28]([OH:30])=[O:29])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58550118methyl 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylate

생성물 1

HCID 585502432-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylic acid수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

To a solution of methyl 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylate (33 g, 57 mmol) in a mixed solvent of tetrahydrofuran (165 ml) and methanol (165 ml) was added 4 N aqueous sodium hydroxide solution (71 ml, 284 mmol), and the mixture was heated at 60° C. for 2 hr. After cooling, the reaction mixture was concentrated, 10% aqueous citric acid solution was added to the residue to adjust the pH to 5, and the mixture was extracted with ethyl acetate. Then, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (31 g, yield 97%).

후처리

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. addition10% aqueous citric acid solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThen, the organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customSodium sulfate was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5dba88e0fa7649a1a7f405f491375545
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299070B2

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