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

HRID 1715833

Reaktionsgleichung

Reaktionsgleichung von HRID 1715833
[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]

Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d3ba2167a67740f1821f85c78f6baf63
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799933B2

Verknüpfte Notizen

Wird geladen…