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

HRID 1715833Notes

Reaction equation

HRID 1715833 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d3ba2167a67740f1821f85c78f6baf63
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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