Sodium Hydroxide → AZD 8329

HRID 1799372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799372
[OH-].[Na+].[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=3)[C:20]=1[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:15])[CH2:10]2>CO>[CH:3]12[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)[C:20]=1[C:21]([CH3:23])([CH3:24])[CH3:22])=[O:15])[CH2:12]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59516081HCID 59516081, Verbindung2×

Produkt 1

HCID 25006684AZD 8329Ausbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2M aqueous sodium hydroxide solution (51.7 mL, 103.32 mmol) was added to methyl 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoate (Intermediate #56) (4.5 g, 10.33 mmol) in methanol (100 mL). The mixture was stirred at 70° C. for 1 hour and then cooled to ambient temperature, concentrated under reduced pressure and diluted with water (100 mL). The reaction mixture was adjusted to pH 3 with 2M HCl. The reaction mixture was extracted with EtOAc (500 mL) and washed to sequentially with water (2×100 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to give a pale yellow solid. The solid was washed with EtOAc (20 mL), collected by filtration and dried under vacuum to give 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoic acid (3.89 g, 89%) as a cream crystalline solid.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water (100 mL)
  4. extractionThe reaction mixture was extracted with EtOAc (500 mL)
  5. washwashed to sequentially with water (2×100 mL), and saturated brine (50 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a pale yellow solid
  10. washThe solid was washed with EtOAc (20 mL)
  11. filtrationcollected by filtration
  12. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5ded6b6b10b54e39b396048a5d488c9b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344016B2

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