Hydrochloric Acid → (8E)-8-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-8-phenyloctanoic acid

HRID 584514Notes

Reaction equation

HRID 584514 reaction equation
O.[OH-].[Li+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:43])=[C:12]([CH2:14][O:15][C:16]2[CH:42]=[CH:41][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:18][CH:17]=2)[N:13]=1.O.Cl>O1CCCC1.C(O)C>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:43])=[C:12]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][O:21]/[N:22]=[C:23](/[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:41][CH:42]=2)[N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22344599ethyl (8E)-8-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-8-phenyloctanoate

Product 1

HCID 22344631(8E)-8-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-8-phenyloctanoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (143 mg) was added to a solution of ethyl E-8-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-8-phenyloctanoate (618 mg) in tetrahydrofuran (6 ml)-water (4 ml)-ethanol (4 ml) and stirred at room temperature for 4 hours. 1N hydrochloric acid (3.5 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-8-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-8-phenyloctanoic acid (523 mg, yield 90%) as colorless crystals. m.p. 75-77° 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-566f10c1995e4512b62e6ee0a9ae897c
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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