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Succinic anhydride → 4-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]--4-oxo-butanoic acid

HRID 703226
ノート
印刷プレビュー

反応式

HRID 703226 の反応式
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][NH:20][OH:21])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1.C([O-])(=O)C.[Na+]>O1CCOCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][N:20]([OH:21])[C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 7922Succinic anhydrideHCID 517045Sodium AcetateHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

生成物 1

HCID 150273944-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]--4-oxo-butanoic acid収率 44%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒
HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

According to the procedure of Example 62, 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine is reacted with 1.0 eq of succinic anhydride in dioxane/water (2:1) in the presence of sodium acetate (2.5 eq). The reaction mixture is diluted with ethyl acetate and is washed with dilute aqueous HCl and then with water. The crude product is purified by recrystallization from methylene chloride. The compound is dissolved in a minimal amount of methanol, diluted with water and lyophylized to give pure 4-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]-4-oxo-butanoic acid (44%); mp 134°-136° C.

後処理

  1. washis washed with dilute aqueous HCl
  2. customThe crude product is purified by recrystallization from methylene chloride
  3. dissolutionThe compound is dissolved in a minimal amount of methanol
  4. additiondiluted with water

出典と根拠

ORDレコード
ord-fb3b1b9fa93a4b29998eb10cc53cb66f
出典データセット
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04981865

反応ノート

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