Sulfuric Acid → Tesaglitazar

HRID 432073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432073
[CH2:1]([O:3][C@@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][S:34]([CH3:37])(=[O:36])=[O:35])=[CH:29][CH:28]=2)=[CH:20][CH:19]=1)[C:5](N[C@H](C1C=CC=CC=1)CO)=[O:6])[CH3:2].S(=O)(=O)(O)[OH:39].O1CCOCC1>O>[CH2:1]([O:3][C@@H:4]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][S:34]([CH3:37])(=[O:35])=[O:36])=[CH:31][CH:32]=2)=[CH:22][CH:23]=1)[C:5]([OH:6])=[O:39])[CH3:2]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 20670106HCID 20670106, Verbindung

Produkt 1

HCID 208901TesaglitazarAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

(S)-2-Ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic amide (4.49 g; 8.59 mmole), concentrated sulfuric acid (12.5 ml), dioxan (50 ml) and water (50 ml) were stirred at 80° C. for 6 hours. After cooling, water (100 ml) was added and the product was extracted with dichloromethane (2×100 ml). The organic phases were combined and washed with brine (60 ml), dried (sodium sulfate), filtered and evaporated in vacuo. Purification by chromatography on silica gel using heptan:ethyl acetate:acetic acid (10:10:1) as gradient and azeotropic destination with toluen gave 2.78 g (yield 79%) of (S)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl} ethoxy)phenyl]propanoic acid.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe product was extracted with dichloromethane (2×100 ml)
  3. washwashed with brine (60 ml)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b1686815c63040978b06fbf92b4e403d
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660879B2

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