Hippuric Acid → Tolterodine Hippurate

HRID 384425

Reaktionsgleichung

Reaktionsgleichung von HRID 384425
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:9][CH2:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:7]=1.[C:25]([OH:37])(=[O:36])[CH2:26][NH:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>CC(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:9][CH2:10][N:11]([CH:12]([CH3:14])[CH3:13])[CH:15]([CH3:16])[CH3:17])[CH:7]=1.[C:25]([O-:37])(=[O:36])[CH2:26][NH:27][C:28]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:29]

Komponenten

4

Edukt 2

HCID 464Hippuric AcidHCID 443879Tolterodine

Produkt 1

HCID 86649494Tolterodine HippurateAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

3.25 g of tolterodine dissolved in 50 mL of acetone was mixed at room temperature (25° C.) with 1.79 g of hippuric acid, which was suspended in 50 mL of acetone, and then stirred. Acetone in the above mixture was removed by nitrogen reflux apparatus, and when about 10 20 mL of acetone was removed there started to appear a solid precipitate. After stirring the mixture at room temperature (25° C.) for 1 hour, the solid precipitate was filtered and then washed with hexane. The resultant was dried at room temperature (25° C.) for 24 hours and 4.66 g (theoretical yield: 92.3%) of the final product in white solid was obtained.

Aufarbeitung

  1. customAcetone in the above mixture was removed by nitrogen
  2. temperaturereflux apparatus, and when about 10 20 mL of acetone
  3. customwas removed there
  4. stirringAfter stirring the mixture at room temperature (25° C.) for 1 hour
  5. filtrationthe solid precipitate was filtered
  6. washwashed with hexane
  7. customThe resultant was dried at room temperature (25° C.) for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-ea1a559b6c2d437882f841f4acd31db6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367726B2

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