Hydrochloric Acid → 3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionic acid

HRID 350098Notes

Reaction equation

HRID 350098 reaction equation
[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH2:19][CH:20](C(OCC)=O)[C:21]([O:23]CC)=[O:22])[C:16]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:16]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23024848diethyl 2-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-ylmethyl]malonate

Product 1

HCID 694216703-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of diethyl 2-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-ylmethyl]malonate (9.41 g), 4N aqueous potassium hydroxide solution (30 ml), and ethanol (30 ml) was refluxed for 1 hour. The reaction mixture was acidified with dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was dissolved in pyridine (20 ml), which was stirred at 110° C. for 2 hours. After removal of the solvent under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, then with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The crystals obtained were collected by filtration to yield 3-[1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionic acid (7.52 g, yield: 99%). This was recrystallized from ethyl acetate-hexane. Melting point: 147–148° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in pyridine (20 ml)
  7. customAfter removal of the solvent under reduced pressure
  8. extractionthe residue was extracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with dilute hydrochloric acid
  10. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  11. concentrationconcentrated
  12. customThe crystals obtained
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1ac1de3989ef4d0b86aafc4c80600736
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…