Sodium Hydroxide → 1048668-70-7

HRID 1799373Notes

Reaction equation

HRID 1799373 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: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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516081HCID 59516081, compound2×

Product 1

HCID 250066841048668-70-7Yield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
62.5 °C

Procedure

Aqueous sodium hydroxide (2M) (2.5 eq) was added portionwise over 5 minutes to a stirred suspension of methyl 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoate (Intermediate #56) (1.0 eq) in methanol (10 vol) at 20° C. (exotherm 20-27° C.). The resulting suspension was heated to 70° C. (jacket temperature), (batch refluxes approx 60-65° C.) for 1 hour (complete by LCMS). The orange reaction mixture was cooled to 20° C. (solution remained slightly cloudy) and filtered through celite to remove a small amount of solids. The filtrate was then poured into a flange flask and water (25 vol) was added. The mixture was then adjusted to pH 3 with 2M HCl (approx 800-850 ml) (turns very thick). The aqueous was then filtered and the pale yellow solid washed with water, sucked dry overnight, and washed with acetonitrile and finally 1:1 acetonotrile/diethyl ether and dried under vacuum at 50° C. for 72 hours (weekend) to give 4-[4-(2-adamantylcarbamoyl)-5-tertbutyl-pyrazol-1-yl]benzoic acid (80%) as a solid.

Workup

  1. temperatureThe orange reaction mixture was cooled to 20° C. (solution
  2. filtrationfiltered through celite
  3. customto remove a small amount of solids
  4. additionThe filtrate was then poured into a flange flask
  5. additionwater (25 vol) was added
  6. filtrationThe aqueous was then filtered
  7. washthe pale yellow solid washed with water
  8. customsucked dry overnight
  9. washwashed with acetonitrile and finally 1:1 acetonotrile/diethyl ether
  10. customdried under vacuum at 50° C. for 72 hours (weekend)

Sources & evidence

ORD record
ord-4c55537e5c684dd4aae7e40eb53d2b04
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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