Water → (4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid tert-butyl ester

HRID 1715833

반응식

HRID 1715833 반응식
[C:1]([O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[CH:22][NH:23]3)=[CH:19][CH:18]=2)=[O:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([O:41][CH3:42])=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:36]=1>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[CH:22][N:23]3[S:37]([C:35]3[CH:36]=[C:31]([Cl:30])[CH:32]=[CH:33][C:34]=3[O:41][CH3:42])(=[O:38])=[O:39])=[CH:19][CH:18]=2)=[O:16])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 68434833{4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester

생성물 1

HCID 68432753(4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid tert-butyl ester

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매

실험 절차

A solution of {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester (0.20 g, 0.57 mmol) in toluene (2.90 mL) was treated with tetrabutylammonium hydrogensulfate (0.02 g, 0.05 mmol) and a 50% solution of NaOH in water (0.57 mL, 7.12 mmol). After stirring at room temperature for 5 min, 5-chloro-2-methoxybenzenesulfonyl chloride (0.21 g, 0.85 mmol) was added. The mixture was stirred for 2 hours, then poured over ice. The resulting slurry was extracted with ethyl acetate and the combined organic phases washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient) to yield (4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid tert-butyl ester as a light yellow oil, 0.26 g (81%), MS (ISP): m/e=555.2 (M+H).

후처리

  1. stirringThe mixture was stirred for 2 hours
  2. additionpoured over ice
  3. extractionThe resulting slurry was extracted with ethyl acetate
  4. washthe combined organic phases washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by flash chromatography (heptane/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-d3ba2167a67740f1821f85c78f6baf63
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799933B2

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