Sodium Hydroxide → HCID 73292407, compound

HRID 1398033Notes

Reaction equation

HRID 1398033 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=2)=[CH:12][C:11]([CH:25]2[CH2:30][C:29]([CH3:32])([CH3:31])[O:28][C:27]([CH3:34])([CH3:33])[CH2:26]2)=[N:10]1.[OH-].[Na+]>CO.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[CH:12][C:11]([CH:25]2[CH2:30][C:29]([CH3:32])([CH3:31])[O:28][C:27]([CH3:34])([CH3:33])[CH2:26]2)=[N:10]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 73293440HCID 73293440, compound

Product 1

HCID 73292407HCID 73292407, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-[1-(2-methoxyphenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-benzoate (Example 17) (200 mg, 0.43 mmol) in 3 mL of methanol was added 0.07 mL of 50% NaOH soln (1.30 mmol) and the mixture heated at 50° C. for 8 hrs. The mixture was diluted with 50 mL of EtOAc and washed with 50 mL of 1N HCL and 50 mL of brine. The organic layer was dried over Na2SO4 and concentrated to give 185 mg (93%) of a white solid.

Workup

  1. washwashed with 50 mL of 1N HCL and 50 mL of brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1af343f6263a4db2bbcf595b87b2932b
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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