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

HRID 1160515Notes

Reaction equation

HRID 1160515 reaction equation
[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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516141HCID 59516141, compound

Product 1

HCID 250024244-[4-(2-Adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]-3-methyl-benzoic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-407e89dee38448b5bf19bcf3ff484eaa
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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