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

HRID 1829947Notes

Reaction equation

HRID 1829947 reaction equation
N1C2C(=CC=CC=2)C(CC(=O)C(O)=O)=C1.[OH-:16].[Na+].C([O-])(=O)C(C)=O.[Na+].[OH:25][C:26]([CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)([C:33]([OH:35])=[O:34])[CH2:27][C:28](=O)[C:29]([OH:31])=[O:30].Cl.[NH2:47]O.Cl>C(=O)([O-])[O-].[Na+].[Na+]>[OH:25][C:26]([CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)([C:33]([OH:35])=[O:34])[CH2:27][C:28](=[N:47][OH:16])[C:29]([OH:31])=[O:30]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 803Indole-3-pyruvic acidHCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochlorideHCID 101494604-Hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acidHCID 23662274Sodium pyruvate

Product 1

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

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

After 10.0 g (49.2 mmol) of indole-3-pyruvic acid was added to and dissolved in 98 ml of aqueous saturated sodium carbonate solution, the resulting solution was adjusted to pH 12.4 using aqueous 25% sodium hydroxide solution. After 16.3 g (147.6 mmol) of sodium pyruvate was added for reaction at ambient temperature for 2 hours, a reaction solution containing 4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid was obtained. 13.7 g (197 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 agitated 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 5.51 g of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid (16.2 mmol; a yield of 32% vs. indole-3-pyruvic acid) in crystal form.

Workup

  1. customwas obtained
  2. extractionto extract the organic matter in ethyl acetate
  3. washThe organic layer was rinsed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationsubsequently concentrated
  6. customto obtain the residue
  7. customThe residue was recrystallized in aqueous 28% ammonia and ethanol

Sources & evidence

ORD record
ord-80c90c640e244b65be68a396c72a785e
Source dataset
uspto-grants-2006_06
Patent number
US07064219B2

Reaction notes

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