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

HRID 1070166Notes

Reaction equation

HRID 1070166 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-α]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 E4-[4-(imidazo[1,2-α]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-4cb1d427c418490899525bc6b7f9f8c0
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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