Sodium Hydroxide → 4-[4-(2-Adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-3-methyl-benzoic acid

HRID 1160515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160515
[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:35]=[CH:34][C:28]([C:29]([O:31]CC)=[O:30])=[CH:27][C:26]=3[CH3:36])[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:35]=[CH:34][C:28]([C:29]([OH:31])=[O:30])=[CH:27][C:26]=3[CH3:36])[C:20]=1[C:21]([CH3:23])([CH3:24])[CH3:22])=[O:15])[CH2:12]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59516141HCID 59516141, Verbindung

Produkt 1

HCID 250024244-[4-(2-Adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-3-methyl-benzoic acidAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of Sodium hydroxide (1.904 mL, 3.81 mmol) was added in one portion to a stirred solution of ethyl 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-3-methyl-benzoate (Intermediate#113) (353 mg, 0.76 mmol) in methanol (6 mL). The resulting suspension was stiffed at 20° C. for 16 hours. The resulting mixture was evaporated to remove the methanol and washed with ether (20 mL). The reaction mixture was acidified with 2M HCl. The precipitate was collected by filtration, washed with water (10 mL) and dried under vacuum to afford 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-3-methyl-benzoic acid (266 mg, 80%) as a white solid.

Aufarbeitung

  1. customThe resulting mixture was evaporated
  2. customto remove the methanol
  3. washwashed with ether (20 mL)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (10 mL)
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-407e89dee38448b5bf19bcf3ff484eaa
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816391B2

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