Hydrochloric Acid → HCID 87950442, compound

HRID 2299851Notes

Reaction equation

HRID 2299851 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH3:40])(/[C:10](=[N:17]\[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27]N2C=C(C)OC2C2C=CC=CC=2)=[CH:22][CH:21]=1)/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6].O.Cl.[O:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1>CO>[CH3:40][C:4]([CH3:3])(/[C:10](=[N:17]\[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:10]2[N:17]=[C:47]([C:46]3[CH:16]=[CH:11][CH:12]=[CH:44][CH:45]=3)[O:43][C:4]=2[CH3:3])=[CH:22][CH:21]=1)/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 22344607HCID 22344607, compound

Product 1

HCID 87950442HCID 87950442, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (1.83 g) was added to a solution of ethyl Z-2,2-dimethyl-3-[4-(5-methyl-2-phenyl-3-oxazolylmethoxy)benzyloxyimino]-3-phenylpropionate (265 mg) in tetrahydrofuran (3 ml)-water (3 ml)-methanol (6 ml), the mixture was heated to reflux for 3 days and cooled to room temperature. Dilute hydrochloric acid 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 remaining crystals were recrystallized from ethyl acetate-hexane to obtain Z-2,2-dimethyl-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-3-phenylpropionic acid (130 mg, yield 52%) as pale-yellow crystals. m.p. 142-143° C. (decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 days
  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
  7. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1cdf27f73edb4eada94a90f118261274
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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