Sodium Hydroxide → HCID 22228131, compound

HRID 1744588Notes

Reaction equation

HRID 1744588 reaction equation
C([CH:3]([C:38]([OH:40])=[O:39])[N:4]([C:19]([C:21]1[C:22]([CH3:37])=[N:23][N:24]([C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=2[Cl:36])[CH:25]=1)=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:7]([C:17]#[N:18])[CH:6]=1)C.[OH-].[Na+]>C(O)C>[Cl:36][C:27]1[CH:28]=[CH:29][C:30]([C:32]([F:34])([F:35])[F:33])=[CH:31][C:26]=1[N:24]1[CH:25]=[C:21]([C:19]([N:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[C:7]([C:17]#[N:18])[CH:6]=2)[CH2:3][C:38]([OH:40])=[O:39])=[O:20])[C:22]([CH3:37])=[N:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22227948HCID 22227948, compound

Product 1

HCID 22228131HCID 22228131, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-[1-(2-Chloro-5-trifluoromethylphenyl)-3-methylpyrazol-4-ylcarbonyl]-N-(3-cyano-4-neopentyloxyphenyl)glycine (1.8 g) was added to ethanol (15 ml). 10% aqueous sodium hydroxide solution (15 ml) was added and the mixture was stirred at a refluxing temperature for 30 min. The solvent was evaporated under reduced pressure, and dilute hydrochloric acid was added. 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. A mixed solvent of chloroform-n-hexane was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of diisopropyl ether-n-hexane to give the title compound (1.2 g), melting point: 189–190° C.

Workup

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

Sources & evidence

ORD record
ord-82c5955f96514239927929bd123c00aa
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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