Hydrochloric Acid → 4-Benzyl-4-hydroxy-2-hydroxyiminoglutaric acid

HRID 252663

Reaction equation

HRID 252663 reaction equation
[OH-:1].[K+].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:15]([OH:23])(=[O:22])[CH2:16][C:17](C(O)=O)=O.Cl.[NH2:25]O.Cl>O.C1(C)C=CC=CC=1>[CH2:9]([C:10]([OH:14])([C:11]([OH:13])=[O:12])[CH2:17][C:16](=[N:25][OH:1])[C:15]([OH:23])=[O:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 970Oxaloacetic AcidHCID 997Phenylpyruvic acidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 858482324-Benzyl-4-hydroxy-2-hydroxyiminoglutaric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

After 16.23 g (having a purity of 85% by weight) of potassium hydroxide was dissolved in 45 ml of water, 5.0 g (30.5 mmol) of phenylpyruvic acid and 12.1 g (91.4 mmol) of oxalacetic acid were added to the resulting solution, for reaction at ambient temperature for 24 hours (about pH 13 at the start of the reaction). To the reaction solution was added 8.5 g (121.8 mmol) of hydroxylamine hydrochloride salt, for reaction at ambient temperature for 72 hours. The reaction solution was adjusted to pH 2.6, using 6N hydrochloric acid, and was then extracted in ethyl acetate. The organic layer was rinsed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated to dryness. The resulting residue was recrystallized in 20 ml of ethyl acetate and 80 ml of toluene, to obtain 4.0 g (15.1 mmol) of 4-benzyl-4-hydroxy-2-hydroxyiminoglutaric acid.

Workup

  1. customat the start of the reaction)
  2. customfor reaction at ambient temperature for 72 hours
  3. extractionwas then extracted in ethyl acetate
  4. washThe organic layer was rinsed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customThe resulting residue was recrystallized in 20 ml of ethyl acetate

Sources & evidence

ORD record
ord-1b57a4dd66844868a9660048378c3c02
Source dataset
uspto-grants-2011_01
Patent number
US07868187B2

Linked notes

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