Hydrochloric Acid → (2Z)-2-(4-methoxyphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetic acid

HRID 584424Notes

Reaction equation

HRID 584424 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](=[N:15]/[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:29][C:30]=3[CH3:31])=[CH:20][CH:19]=2)/[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.Cl>O1CCCC1.CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](=[N:15]/[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:29][C:30]=3[CH3:31])=[CH:20][CH:19]=2)/[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22344571ethyl (2Z)-2-(4-methoxyphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetate

Product 1

HCID 11005205(2Z)-2-(4-methoxyphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetic acidYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl Z-2-(4-methoxyphenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (1.20 g) was dissolved in tetrahydrofuran (5 ml)-methanol (10 ml), and 0.5N aqueous solution of sodium hydroxide (10 ml) was added and the mixture was heated under reflux for 1 hour. 1N HCl (5.5 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residual crystal was recrystallized from ethyl acetate to obtain Z-2-(4-methoxyphenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetic acid (1.02 g, yield 90%) as colorless crystals. m.p. 183-184° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residual crystal was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e97a62559fe74f039b77d23198ef52c6
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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