Sodium Hydroxide → HCID 25007441, compound

HRID 1799377Notes

Reaction equation

HRID 1799377 reaction equation
[OH-].[Na+].[F:3][CH:4]([F:38])[O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH:9]3[NH:16][C:17]([C:19]3[CH:20]=[N:21][N:22]([C:28]4[CH:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=4)[C:23]=3[S:24][CH2:25][CH2:26][CH3:27])=[O:18])[CH2:7]1)[CH2:13]2>CO>[F:38][CH:4]([F:3])[O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH:9]3[NH:16][C:17]([C:19]3[CH:20]=[N:21][N:22]([C:28]4[CH:37]=[CH:36][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=4)[C:23]=3[S:24][CH2:25][CH2:26][CH3:27])=[O:18])[CH2:7]1)[CH2:13]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516105HCID 59516105, compound2×

Product 1

HCID 25007441HCID 25007441, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

2M aqueous sodium hydroxide (2.050 mL, 4.10 mmol) was added in one portion to methyl 4-[4-[[5-(difluoromethoxy)-2-adamantyl]carbamoyl]-5-propylsulfanylpyrazol-1-yl]benzoate (Intermediate #95) (459 mg, 0.82 mmol) in methanol (10 mL). The resulting mixture was stirred at 20° C. for 18 hours and then a further 4 hours at 55° C. The reaction mixture was concentrated and diluted with water (50 mL), and washed with ether (20 mL). The aqueous solution was adjusted to pH 3 with 2M HCl and extracted with EtOAc (2×25 mL), and the combined extracts washed sequentially with water (2×20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 4-[4-[[5-(difluoromethoxy)-2-adamantyl]carbamoyl]-5-propylsulfanylpyrazol-1-yl]benzoic acid (284 mg, 63.5%).

Workup

  1. customa further 4 hours
  2. customat 55° C
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with water (50 mL)
  5. washwashed with ether (20 mL)
  6. extractionextracted with EtOAc (2×25 mL)
  7. washthe combined extracts washed sequentially with water (2×20 mL) and saturated brine (20 mL)
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-fe9f262af8ee4647acf5ef649b23ece9
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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