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

HRID 2299780Notes

Reaction equation

HRID 2299780 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-5a27a953875e4e49bc8f39275eed6235
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

Loading…