Acetic Acid → HCID 178519412, compound

HRID 471867Notes

Reaction equation

HRID 471867 reaction equation
CC(C)(C)C(OC[N:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=3)[CH:15]=[CH:16][CH:17]=2)=[N:8]1)=O.[OH-].[Na+].CC(O)=O>C1COCC1.CO>[NH:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=3)[CH:15]=[CH:16][CH:17]=2)=[N:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86641432HCID 86641432, compound

Product 1

HCID 178519412HCID 178519412, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of [3-(4′-formyl-3-biphenylyl)-1H-pyrazol-1-yl]methyl 2,2-dimethyl-propanoate (0.162 g; 0.45 mmol) in 1:1 THF/MeOH (5 mL total vol) at room temperature was added NaOH (1.1 mL of a 1.0M solution; 1.1 mmol). After 30 min, HOAc (0.08 mL; 1.4 mmol) was added and the mixture was concentrated in vacuo. The residue was partitioned between EtOAc/water, layers were separated, the organic layer was washed (satd NaHCO3, brine), dried over Na2SO4 and concentrated in vacuo. The residue was redissolved in EtOAc, washed (1M HCl, water, brine), dried over Na2SO4 and concentrated in vacuo, affording the title compound as a glassy semi-solid which was used without further purification. LC/MS (method A) 2.42 min; m/z 249 (M+H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was partitioned between EtOAc/water, layers
  3. customwere separated
  4. washthe organic layer was washed (satd NaHCO3, brine)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was redissolved in EtOAc
  8. washwashed (1M HCl, water, brine)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e47854d6ab246d181e0055850d43bdc
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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