Potassium Hydroxide → HCID 178441712, Verbindung

HRID 889514

Reaktionsgleichung

Reaktionsgleichung von HRID 889514
[OH-].[K+].[CH3:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]3[N:29]=[N:28][N-:27][N:26]=3)=[CH:17][CH:18]=2)[C:10]([CH2:30][OH:31])=[C:9]([Cl:32])[N:8]=1.[K+].I([O-])(=O)(=O)=[O:35].[Na+]>O.[Ru](Cl)(Cl)Cl.O>[CH2:6]([C:7]1[N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:17][CH:18]=2)[C:10]([C:30]([OH:35])=[O:31])=[C:9]([Cl:32])[N:8]=1)[CH2:5][CH2:4][CH3:3]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 11476710Losartan potassium saltHCID 23667635Sodium periodate

Produkt 1

HCID 178441712HCID 178441712, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Water (10 L) was added to a 22 L 4-neck round-bottom flask. The water was cooled to 0° C. At 0° C., potassium hydroxide (855 g, 15.24 mol) was added, followed by losartan potassium (500 g, 1.09 mol), sodium periodate (554 g, 2.59 mol) and ruthenium (III) chloride hydrate (12 g, 0.05 mol), and the reaction mixture was stirred at 0° C. overnight. The reaction mixture was filtered. Isopropanol (90 mL) was added to the filtrate while stirring. The solution was warmed to 25° C. and stirred for 2.5 hours. After 2.5 hours, phosphoric acid (1200 mL) was added, maintaining the temperature below 30° C. The mixture was stirred for 30 minutes and the product was filtered, washing with water. The residue was dried in the vacuum oven at 55° C. overnight. The solid was dissolved in methanol (4 L) and isopropyl acetate (12 L), and charcoal (activated carbon) (100 g) was added. The mixture was stirred at room temperature for 3.5 hours, filtered and concentrated. The product was redissolved in dichloromethane/methanol and precipitated with heptane to afford the title compound as a greenish brown foam, which was used in the subsequent step without further purification.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additionIsopropanol (90 mL) was added to the filtrate
  3. stirringwhile stirring
  4. temperatureThe solution was warmed to 25° C.
  5. stirringstirred for 2.5 hours
  6. waitAfter 2.5 hours
  7. additionphosphoric acid (1200 mL) was added
  8. temperaturemaintaining the temperature below 30° C
  9. stirringThe mixture was stirred for 30 minutes
  10. filtrationthe product was filtered
  11. washwashing with water
  12. customThe residue was dried in the vacuum oven at 55° C. overnight
  13. dissolutionThe solid was dissolved in methanol (4 L)
  14. additionisopropyl acetate (12 L), and charcoal (activated carbon) (100 g) was added
  15. stirringThe mixture was stirred at room temperature for 3.5 hours
  16. filtrationfiltered
  17. concentrationconcentrated
  18. dissolutionThe product was redissolved in dichloromethane/methanol
  19. customprecipitated with heptane

Quellen und Nachweise

ORD-Eintrag
ord-ef3047e6441540129c56675651b3de23
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252825B2

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