Sulfuric Acid → 1-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester

HRID 342808ノート

反応式

HRID 342808 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])OCC[O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].S(=O)(=O)(O)O>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16](=[O:17])[CH3:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 675985121-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

生成物 1

HCID 675993131-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester収率 59.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of crude 1-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester (2.85 g, ≈5 mmol) in acetone (60 ml) was added concentrated sulfuric acid (0.6 ml). The solution was stirred at room temperature for about 45 minutes, and most of the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (silica, 130 g) eluting with a gradient from 30% -ethyl acetate/hexane to 40% ethyl acetate/hexane, to give the title compound (1.48 g).

後処理

  1. custommost of the solvent was removed under reduced pressure
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica, 130 g)
  6. washeluting with a gradient from 30% -ethyl acetate/hexane to 40% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-8f2bc46890764eacaba2817c227374ca
出典データセット
uspto-grants-1999_01
特許番号
US05859044

反応ノート

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