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

HRID 584482
Notes
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Reaction equation

HRID 584482 reaction equation
O.[OH-].[Li+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:38])=[C:12]([CH2:14][O:15][C:16]2[CH:37]=[CH:36][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)\[CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:18][CH:17]=2)[N:13]=1.O.Cl>O1CCCC1.CO>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:38])=[C:12]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)\[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:36][CH:37]=2)[N:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 11091963methyl (4E)-4-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 10885020(4E)-4-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoic acidYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (76.0 mg) was added to a solution of methyl E-4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-4-phenylbutyrate (430 mg) in tetrahydrofuran (6 ml)-water (4 ml)-methanol (4 ml) and stirred at room temperature for 2 hours. 1N hydrochloric acid (1.9 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-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-4-phenylbutyric acid (328 mg, yield 79%) as colorless crystals. m.p. 124-125° 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-394df939a49a4ddea283ec165983b26c
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06924300B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes