Dimethyl Sulfoxide → Mitoglitazone

HRID 1756628ノート

反応式

HRID 1756628 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 10429242Mitoglitazone収率 20%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-afdb7ea8915e42ada94ab982fa99b1d6
出典データセット
uspto-grants-1995_08
特許番号
US05441971

反応ノート

読み込み中…