Sulfuric Acid → Tesaglitazar

HRID 1384419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384419
[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 destillation 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-2a137a69a1fa4a00a41be2e3f8bda3b9
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258850B1

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