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

HRID 1030371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030371
[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]

Komponenten

4

Edukt 2

HCID 5591TroglitazoneHCID 7922Succinic anhydride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a16edc0a0af94d99abb80a245c6b1ca3
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104888

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