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

HRID 1070163Notes

Reaction equation

HRID 1070163 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

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 E4-[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-7bc3c502820540509ac09421f6647669
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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