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

HRID 1715833

反応式

HRID 1715833 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d3ba2167a67740f1821f85c78f6baf63
出典データセット
uspto-grants-2010_09
特許番号
US07799933B2

関連ノート

読み込み中…