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

HRID 584467Notes

Reaction equation

HRID 584467 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:36]=[CH:37][CH:38]=1)[CH2:20][O:21]/[N:22]=[C:23](/[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)\[CH2:24][CH2:25][C:26]([O:28]C)=[O:27].CO.Cl>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:36]=[CH:37][CH:38]=1)[CH2:20][O:21]/[N:22]=[C:23](/[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)\[CH2:24][CH2:25][C:26]([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 11762628methyl (4E)-4-[[3-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 10917674(4E)-4-[[3-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous saturated solution of sodium hydroxide (5 ml) was added to a solution of methyl E-4-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (500 mg) in tetrahydrofuran (10 ml)-methanol (5 ml) and stirred at room temperature for 1 hour. 1N hydrochloric acid (5.5 ml) was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain E-4-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyric acid (395 mg, yield 82%) as colorless crystals. m.p. 108-109° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-03343f371be54371b98a4fd88ee2c6d0
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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