Potassium Hydroxide → HCID 178441712, Verbindung

HRID 222527

Reaktionsgleichung

Reaktionsgleichung von HRID 222527
[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. IPA (90 mL) was added to the filtrate while stirring. The solution was warmed to 25° C. and stirred for 2.5 hrs. After 2.5 hrs., phosphoric acid (1200 mL) was added, maintaining the temperature below +30° C. The mixture was stirred for 30 min 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 rt for 3.5 hrs, filtered and concentrated. The product was redissolved in DCM/MeOH and precipitated with heptane to afford the title compound as a greenish/brown foam which was used in subsequent steps without further purification.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additionIPA (90 mL) was added to the filtrate
  3. stirringwhile stirring
  4. temperatureThe solution was warmed to 25° C.
  5. stirringstirred for 2.5 hrs
  6. waitAfter 2.5 hrs
  7. addition, phosphoric acid (1200 mL) was added
  8. temperaturemaintaining the temperature below +30° C
  9. stirringThe mixture was stirred for 30 min
  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 rt for 3.5 hrs
  16. filtrationfiltered
  17. concentrationconcentrated
  18. dissolutionThe product was redissolved in DCM/MeOH
  19. customprecipitated with heptane

Quellen und Nachweise

ORD-Eintrag
ord-c9c6c11d3fbe4c8390c20be67ccc84e3
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207208B2

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