Sodium Hydroxide → HCID 25007798, compound

HRID 1799378Notes

Reaction equation

HRID 1799378 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:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)[C:20]=1[S:21][CH2:22][CH3:23])=[O:15])[CH2:10]2>CO>[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:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)[C:20]=1[S:21][CH2:22][CH3:23])=[O:15])[CH2:10]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516090HCID 59516090, compound2×

Product 1

HCID 25007798HCID 25007798, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

2M aqueous sodium hydroxide (2.446 mL, 4.89 mmol) was added in one portion to methyl 4-[4-(2-adamantylcarbamoyl)-5-ethylsulfanyl-pyrazol-1-yl]benzoate (Intermediate #99) (430 mg, 0.98 mmol) in methanol (20 mL). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was concentrated, diluted with water (50 mL) and adjusted to pH 3 with 2M HCl. The precipitate was collected by filtration, washed with water (20 mL) and dried under vacuum to afford 4-[4-(2-adamantylcarbamoyl)-5-ethylsulfanyl-pyrazol-1-yl]benzoic acid (383 mg, 92%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (50 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (20 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e8d68df012bf4ac7a1109776821184da
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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