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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
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인쇄 미리보기

반응식

HRID 703226 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb3b1b9fa93a4b29998eb10cc53cb66f
출처 데이터셋
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04981865

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