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Sodium Hydroxide → 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoic acid

HRID 541452
Notes
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Reaction equation

HRID 541452 reaction equation
[CH:1]1([C:5]2[C:14]([C:15]3[CH:19]=[C:18]([CH2:20][CH3:21])[NH:17][N:16]=3)=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:5]2[C:14]([C:15]3[CH:19]=[C:18]([CH2:20][CH3:21])[NH:17][N:16]=3)=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68288367methyl 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoate2×

Product 1

HCID 682887464-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoate (compound 445.2, 188 mg, 0.630 mmol, 1.00 equiv) in methanol (6 mL) was added aqueous sodium hydroxide (76.0 mg, 1.90 mmol, 3.00 equiv in 3 mL water). The resulting solution was stirred for 2 h at 70° C. in an oil bath. After cooling to ambient temperature, the mixtue was concentrated under reduced pressure. The residue was diluted with 20 mL of H2O. The pH of the mixture was adjusted to −4 with aqueous HCl (2 M). The mixture was then extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with 3×20 mL of brine, dried (Na2SO4), and concentrated under reduced pressure. This resulted in 0.180 g (crude) of the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixtue was concentrated under reduced pressure
  3. additionThe residue was diluted with 20 mL of H2O
  4. extractionThe mixture was then extracted with 3×20 mL of ethyl acetate
  5. washThe combined organic layers were washed with 3×20 mL of brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce8a0638316147a6988935ccf160b2e4
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871790B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes