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

HRID 133673

Reaction equation

HRID 133673 reaction equation
N1C2C(=CC=CC=2)C(CC(=O)C(O)=O)=C1.[OH-:16].[Na+].C(O)(=O)C(C)=O.[OH:24][C:25]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)([C:32]([OH:34])=[O:33])[CH2:26][C:27](=O)[C:28]([OH:30])=[O:29].Cl.[NH2:46]O.Cl>C(=O)([O-])[O-].[Na+].[Na+]>[OH:24][C:25]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)([C:32]([OH:34])=[O:33])[CH2:26][C:27](=[N:46][OH:16])[C:28]([OH:30])=[O:29]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 803Indole-3-pyruvic acidHCID 1060Pyruvic AcidHCID 14798Sodium Hydroxide3×HCID 443297Hydroxyamine hydrochlorideHCID 101494604-Hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

Product 1

HCID 589060822-Hydroxy-4-(hydroxyimino)-2-[(1H-indol-3-yl)methyl]pentanedioic acid

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

After 1.0 g (4.92 mmol) of indole-3-pyruvic acid was added to and dissolved in 10 ml of aqueous saturated sodium carbonate solution, the resulting solution was adjusted to pH 12.55 using aqueous 25% sodium hydroxide solution. After 1.3 g (14.8 mmol) of pyruvic acid was added, the resulting solution was adjusted to pH 12.6 using aqueous 25% sodium hydroxide solution, for reaction at ambient temperature for 2 hours, to obtain a reaction solution containing 4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid. 1.37 g (19.7 mmol) of hydroxylamine hydrochloride salt was added to the reaction solution, while the reaction solution was adjusted to a pH value around neutrality using aqueous 25% sodium hydroxide solution, and stirred at ambient temperature for 4 hours. Using conc. hydrochloric acid, the reaction solution was adjusted to an acidic pH value, to extract the organic matter in ethyl acetate. The organic layer was rinsed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and subsequently concentrated, to obtain the residue. The residue was recrystallized in aqueous 28% ammonia and ethanol, to obtain 0.52 g of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid (1.5 mmol; a yield, 31% vs. indole-3-pyruvic acid) in crystal form.

Workup

  1. customfor reaction at ambient temperature for 2 hours
  2. customto obtain a reaction solution
  3. extractionto extract the organic matter in ethyl acetate
  4. washThe organic layer was rinsed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationsubsequently concentrated
  7. customto obtain the residue
  8. customThe residue was recrystallized in aqueous 28% ammonia and ethanol

Sources & evidence

ORD record
ord-5b1f893879d748b084ee61b6e20dec91
Source dataset
uspto-grants-2008_06
Patent number
US07390909B2

Linked notes

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