1,4-Dioxane → N-methyl-N-phenethyl-2-[5-benzyloxy-1-(2-carbethoxyvinyl)indol-3-yl]acetamide

HRID 129688ノート

反応式

HRID 129688 の反応式
[CH3:1][N:2]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3](=[O:22])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][CH:6]=1.[OH-:31].C([N+](C)(C)C)[C:33]1[CH:38]=[CH:37]C=CC=1.C1C=CC(C2C=CC(NC3C=CC=CC=3)=CC=2)=CC=1.[O:62]1CCO[CH2:64][CH2:63]1>>[CH3:1][N:2]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:3](=[O:22])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[N:7]([CH:37]=[CH:38][C:33]([O:62][CH2:63][CH3:64])=[O:31])[CH:6]=1

参加物

5

反応物 4

HCID 312751,4-DioxaneHCID 66854Benzyltrimethylammonium hydroxideHCID 13087229N-phenyl-(1,1'-biphenyl)-4-amineHCID 19372283N-methyl-N-phenethyl-2-(5-benzyloxyindol-3-yl)acetamide

生成物 1

HCID 54482929N-methyl-N-phenethyl-2-[5-benzyloxy-1-(2-carbethoxyvinyl)indol-3-yl]acetamide

実験手順

To a mixture of 1.579 g (3.96 mmol) of N-methyl-N-phenethyl-2-(5-benzyloxyindol-3-yl)acetamide and 0.4 ml of benzyltrimethylammonium hydroxide (40% solution in methanol) in 15 ml of dioxane is added with stirring 0.44 ml (0.43 g, 4.35 mmol) of ethyl propriolate. A reddish solution is obtained, which is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is taken up in ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by dry column chromatography over silica gel eluting with a solvent system of 5% ethyl acetate in methylene chloride to yield 450 mg of N-methyl-N-phenethyl-2-[5-benzyloxy-1-(2-carbethoxyvinyl)indol-3-yl]acetamide.

後処理

  1. additionis added
  2. customA reddish solution is obtained
  3. concentrationconcentrated in vacuo
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified
  8. dry with materialby dry column chromatography over silica gel eluting with a solvent system of 5% ethyl acetate in methylene chloride

出典と根拠

ORDレコード
ord-5d5e73cb61e64b33ad77920a61d0ab71
出典データセット
uspto-grants-1995_11
特許番号
US05468898

反応ノート

読み込み中…