Hydrochloric Acid → (6E)-2,2-dimethyl-6-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-6-phenylhexanoic acid

HRID 584526Notes

Reaction equation

HRID 584526 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH3:42])([CH2:9][CH2:10][CH2:11]/[C:12](=[N:19]\[O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:24][CH:23]=1)/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([O:7]C)=[O:6].CO.Cl>O1CCCC1>[CH3:3][C:4]([CH3:42])([CH2:9][CH2:10][CH2:11]/[C:12](=[N:19]\[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:26][CH:27]=1)/[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 11145964methyl (6E)-2,2-dimethyl-6-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-6-phenylhexanoate

Product 1

HCID 11005907(6E)-2,2-dimethyl-6-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-6-phenylhexanoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 4N aqueous solution of potassium hydroxide (5 ml) was added to a solution of methyl E-2,2-dimethyl-6-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-6-phenylhexanoate (340 mg) in tetrahydrofuran (5 ml)-methanol (5 ml), which was heated to reflux for 2 hours and cooled to room temperature. Dilute hydrochloric acid was added to the reaction mixture to neutralize 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 subjected to silica gel chromatography to obtain E-2,2-dimethyl-6-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-6-phenylhexanoic acid (275 mg, yield 83%) as colorless crystals. m.p. 111-112° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6e059c2220694c7ca986ad89eef09219
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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