Hydrochloric Acid → [3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethoxy]-1-phenyl-1H-pyrazol-4-yl]acetic acid

HRID 1295328Notes

Reaction equation

HRID 1295328 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[N:20]=[CH:19][C:18]([CH2:21][O:22][C:23]2[C:27]([CH2:28][C:29]([O:31]C)=[O:30])=[CH:26][N:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:24]=2)=[CH:17][CH:16]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21][O:22][C:23]2[C:27]([CH2:28][C:29]([OH:31])=[O:30])=[CH:26][N:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:24]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86591687methyl [3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethoxy]-1-phenyl-1H-pyrazol-4-yl]acetate

Product 1

HCID 10278420[3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethoxy]-1-phenyl-1H-pyrazol-4-yl]acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl [3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethoxy]-1-phenyl-1H-pyrazol-4-yl]acetate (587 mg), 1N aqueous sodium hydroxide solution (3 ml), tetrahydrofuran (6 ml) and ethanol (6 ml) was stirred at room temperature for 1 hr. 1N Hydrochloric acid (3 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were collected by filtration to give [3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethoxy]-1-phenyl-1H-pyrazol-4-yl]acetic acid (502 mg, yield 88%), which was then recrystallized from ethanol-hexane. melting point: 164–165° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-2f3714409d624ffb98d4479873d1a2fb
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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