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

HRID 1070164Notes

Reaction equation

HRID 1070164 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:4][C:3]=1[CH2:12][O:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][O:19]/[N:20]=[C:21](/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)\[CH2:22][CH2:23][C:24]([O-:26])=[O:25])=[CH:16][CH:15]=1.O.CO.Cl>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:4][C:3]=1[CH2:12][O:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][O:19]/[N:20]=[C:21](/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)\[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 21191191(4E)-4-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 10939713(4E)-4-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

E-4-[4-[5-methyl-2-(2-thienyl)-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 (1.8 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-[5-methyl-2-(2-thienyl)-4-oxazolylmethoxy]benzyloxyimino]-4-phenylbutyric acid (366 mg, yield 88%) as colorless crystals. m.p. 142-143° 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-f9a642fee5b34b53a92a76753dc45c81
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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