Hydrochloric Acid → HCID 69422240, compound

HRID 350114Notes

Reaction equation

HRID 350114 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:46]=[CH:45][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH:28](C(OCC)=O)[C:29]([O:31]CC)=[O:30])[C:22]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:21]2)=[CH:17][CH:16]=1.[OH-].[K+].Cl>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:46]=[CH:45][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:22]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[N:21]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69423290HCID 69423290, compound

Product 1

HCID 69422240HCID 69422240, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of diethyl 2-[3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propyl]malonate (1.56 g), 4N aqueous potassium hydroxide solution (5 ml) and ethanol (10 ml) was refluxed for 30 minutes. 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. A mixture of the residue and pyridine (10 ml) was stirred at 110° C. for 2 hours. After removal of the solvent under reduced pressure, the mixture 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 colorless crystals obtained were collected by filtration to yield 5-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]pentanoic acid (857 mg, yield: 65%). This was recrystallized from ethyl acetate-hexane. Melting point: 109–110° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  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. additionA mixture of the residue and pyridine (10 ml)
  7. customAfter removal of the solvent under reduced pressure
  8. extractionthe mixture 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 colorless crystals obtained
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-048b2df0e757493ca19d3610c52244c3
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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