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

HRID 2244788

Reaktionsgleichung

Reaktionsgleichung von HRID 2244788
[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

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cc5b9ca612844d499057c045b0c055b9
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678925B2

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