Hydrochloric Acid → (4E)-4-[[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl]methoxyimino]-4-phenylbutanoic acid

HRID 584488Notes

Reaction equation

HRID 584488 reaction equation
O.[OH-].[Li+].[N:4]1[C:5]([CH2:13][O:14][C:15]2[CH:36]=[CH:35][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)\[CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:17][CH:16]=2)=[CH:6][N:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12.O.Cl>O1CCCC1.CO>[N:4]1[C:5]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)\[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:35][CH:36]=2)=[CH:6][N:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22344637methyl (4E)-4-[[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl]methoxyimino]-4-phenylbutanoate

Product 1

HCID 87950457(4E)-4-[[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl]methoxyimino]-4-phenylbutanoic acidYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (53.0 mg) was added to a solution of methyl E-4-[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (280 mg) in tetrahydrofuran (6 ml)-water (4 ml)-methanol (4 ml) and stirred at room temperature for 2 hours. 1N hydrochloric acid (1.3 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-(imidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyric acid (206 mg, yield 76%) as colorless crystals. m.p. 180-182° 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-9d6e897fe2f7494f9158ff735220a9cf
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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