Troglitazone → 2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-2,5,7,8-tetramethylchroman-6-yl hydrogen succinate

HRID 1030371ノート

反応式

HRID 1030371 の反応式
[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2.[C:32]1(=[O:38])[O:37][C:35](=[O:36])[CH2:34][CH2:33]1>N1C=CC=CC=1>[C:32]([O:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2)(=[O:38])[CH2:33][CH2:34][C:35]([OH:37])=[O:36]

参加物

4

反応物 2

HCID 5591TroglitazoneHCID 7922Succinic anhydride

生成物 1

HCID 179941992-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-2,5,7,8-tetramethylchroman-6-yl hydrogen succinate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 1.0 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine -2,4-dione (prepared as described in Example 28), 0.31 g of succinic anhydride and 1 ml of pyridine was allowed to stand overnight at room temperature. The reaction mixture was then washed 3 times, each time with 10 ml of cyclohexane, and the insoluble residue obtained was purified by silica gel column chromatography (eluted by mixtures of benzene and ethyl acetate ranging from 5:1 to 1:1) to give the title compound melting at 197°-202° C.

後処理

  1. washThe reaction mixture was then washed 3 times
  2. customeach time with 10 ml of cyclohexane, and the insoluble residue obtained
  3. customwas purified by silica gel column chromatography (eluted by mixtures of benzene and ethyl acetate ranging from 5:1 to 1:1)

出典と根拠

ORDレコード
ord-a16edc0a0af94d99abb80a245c6b1ca3
出典データセット
uspto-grants-1992_04
特許番号
US05104888

反応ノート

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