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

HRID 584479
Notes
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Reaction equation

HRID 584479 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][O:23]/[N:24]=[C:25](/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)\[CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:20][CH:19]=1.O.Cl>O1CCCC1.CO>[CH3:4][C:5]1[S:9][C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:7][C:6]=1[CH2:16][O:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][O:23]/[N:24]=[C:25](/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)\[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 11027498methyl (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 11733632(4E)-4-[[4-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (83.6 mg) was added to a solution of methyl E-4-[4-(5-methyl-2-phenyl-4-thiazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (500 mg) in tetrahydrofuran (10 ml)-water (4 ml)-methanol (8 ml) and stirred at room temperature for 2 hours. 1N hydrochloric acid (2.1 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-phenyl-4-thiazolylmethoxy)benzyloxyimino]-4-phenylbutyric acid (363 mg, yield 75%) as colorless crystals. m.p. 99-100° 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-5c1fcb6e8187436a846ace75d4b376a4
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