Hydrochloric Acid → HCID 87950453, compound

HRID 2299802Notes

Reaction equation

HRID 2299802 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:9]2[CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:36]=[CH:35][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)\[CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:17][CH:16]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.CO.Cl>O1CCCC1>[Cl:3][C:4]1[N:9]2[CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)\[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:35][CH:36]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22344575HCID 22344575, compound

Product 1

HCID 87950453HCID 87950453, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous saturated solution of sodium hydroxide (5 ml) was added to a solution of methyl E-4-[4-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (400 mg) in tetrahydrofuran (10 ml)-methanol (5 ml) and stirred at room temperature for 1 hour. 1N hydrochloric acid (5.5 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-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyric acid (313 mg, yield 78%) as colorless crystals. m.p. 160-161° 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-392840de2aae4f51857b1df9b419b9d4
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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