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Ethanol → 5-[8-Methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 1811443
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인쇄 미리보기

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HRID 1811443 반응식
[OH-].[Li+].C(O)C.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:30][CH:31]2[S:35][C:34](=[O:36])[NH:33][C:32]2=[O:37])=[C:12]2[C:17]=1[N:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=1)[C:15](=[O:29])[CH2:14][CH2:13]2>C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:30][CH:31]2[S:35][C:34](=[O:36])[NH:33][C:32]2=[O:37])=[C:12]2[C:17]=1[N:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=1)[C:15](=[O:29])[CH2:14][CH2:13]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 580267165-[8-Methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

생성물 1

HCID 866139425-[8-Methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione수율 97%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

35 ml of an aqueous 1 N-lithium hydroxide solution was added to a mixed ethanol (200 ml) and THF (200 ml) solution of 4.0 g of 5-[8-methoxy-1-(4-methoxycarbonylbenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione, followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure, hydrochloric acid was added to the residue, and the insoluble matter thus formed was collected by filtration. The collected insoluble matter was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:3), and recrystallized from ethyl acetate, giving 3.75 g (97% yield) of 5-[8-methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione as a white powder.

후처리

  1. distillationThe solvent was distilled off under reduced pressure, hydrochloric acid
  2. additionwas added to the residue
  3. customthe insoluble matter thus formed
  4. filtrationwas collected by filtration
  5. customThe collected insoluble matter was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:3)
  6. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-5223a30293f047a6ab7f8683e7af3ac2
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362252B2

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