Hydrochloric Acid → 2-Hydroxy-4-(hydroxyimino)-2-[(1H-indol-3-yl)methyl]pentanedioic acid

HRID 252662

Reaktionsgleichung

Reaktionsgleichung von HRID 252662
[OH-:1].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13](=[O:17])[C:14]([OH:16])=[O:15])=[CH:4]1.[C:18]([OH:26])(=[O:25])[CH2:19][C:20](C(O)=O)=O.Cl.[NH2:28]O.[OH-].[Na+].Cl>O>[OH:17][C:13]([CH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:3][CH:4]=1)([C:14]([OH:16])=[O:15])[CH2:20][C:19](=[N:28][OH:1])[C:18]([OH:26])=[O:25]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 803Indole-3-pyruvic acidHCID 970Oxaloacetic AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 589060822-Hydroxy-4-(hydroxyimino)-2-[(1H-indol-3-yl)methyl]pentanedioic acidAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

After 13.8 g of potassium hydroxide (having a purity of 85% by weight) was dissolved in 50 ml of water, 5.0 g (24.6 mmol) of indole-3-pyruvic acid and 9.8 g (73.8 mmol) of oxalacetic acid were added to the resulting solution, for reaction at ambient temperature for 72 hours (about pH 13 at the start of the reaction). To the reaction solution was added 6.8 g (98.4 mmol) of hydroxylamine hydrochloride salt. Then, the reaction solution was adjusted to pH 7.5 with aqueous 4N sodium hydroxide solution. After the reaction solution had been stirred for 24 hours at ambient temperature, the reaction solution was adjusted to pH 2.6 with 6N hydrochloric acid. After extraction using ethyl acetate, the organic layer was rinsed in aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated to dryness. The resulting residue was dissolved in 10 ml of aqueous 14% ammonia, followed by gradual dropwise addition of 70 ml of ethanol, and stirred at ambient temperature for 3 hours. The resulting slurry was filtered. The resulting crystals was dried to obtain 2.7 g (7.9 mmol) of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid in the form of an ammonium salt.

Aufarbeitung

  1. customat the start of the reaction)
  2. extractionAfter extraction
  3. washthe organic layer was rinsed in aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. dissolutionThe resulting residue was dissolved in 10 ml of aqueous 14% ammonia
  7. additionfollowed by gradual dropwise addition of 70 ml of ethanol
  8. stirringstirred at ambient temperature for 3 hours
  9. filtrationThe resulting slurry was filtered
  10. customThe resulting crystals was dried

Quellen und Nachweise

ORD-Eintrag
ord-6a8e22fcb41a426ab03cbb3d631146c4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868187B2

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