Dimethyl Sulfoxide → Mitoglitazone

HRID 1756628노트

반응식

HRID 1756628 반응식
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:26])[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].C(O)C.C(OC(=O)C)(=O)C.CS(C)=O>O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:26])[CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:24][CH:25]=2)=[N:7][CH:8]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 7918Acetic AnhydrideHCID 98642685-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

생성물 1

HCID 10429242Mitoglitazone수율 20%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 5-[4-[2-(5-ethyl-2-pyridyl)-2-hydroxyethoxy]benzyl]-2,4-thiazolidinedione. 1/2 C2H5OH (396 mg), acetic anhydride (1.5 ml) and dimethylsulfoxide (4 ml) was stirred at room temperature for 5 hours and then poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate and the solvent was distilled off. The oily residue was subjected to silica gel chromatography. A fraction eluted with chloroform-methanol (100:1, v/v) gave 5-[4-[2-(5-ethyl-2-pyridyl)-2-oxoethoxy]benzyl]-2,4-thiazolidinedione (75 mg, yield: 20%). This was recrystallized from ethyl acetate-hexane to obtain colorless prisms, m.p. 148°-149° C.

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washA fraction eluted with chloroform-methanol (100:1

출처 및 근거

ORD 기록
ord-afdb7ea8915e42ada94ab982fa99b1d6
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05441971

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