Sodium Hydroxide → 4-[N-(3-Cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetic acid

HRID 1744580Notes

Reaction equation

HRID 1744580 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[C:19]([CH3:29])=[N:20][N:21]([CH2:23][C:24]([O:26]CC)=[O:25])[CH:22]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[C:19]([CH3:29])=[N:20][N:21]([CH2:23][C:24]([OH:26])=[O:25])[CH:22]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22228013Ethyl 4-[N-(3-cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetate

Product 1

HCID 222282094-[N-(3-Cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetic acidYield 30.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-[N-(3-cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetate (0.7 g) was added to ethanol (5 ml) and 10% aqueous sodium hydroxide solution (5 ml) was added. The mixture was stirred at a refluxing temperature for 30 min. The solvent was evaporated under reduced pressure. To the residue was added dilute hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether to give the title compound (0.2 g), melting point: 234–245° C.

Workup

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. additionTo the residue was added dilute hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was evaporated under reduced pressure
  8. additionDiisopropyl ether was added to the residue
  9. customcrystallization
  10. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-45712526133a4423a9e7690273262fbb
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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