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

HRID 252669

反応式

HRID 252669 の反応式
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]

参加物

8

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1763d007c3da42999ba6c0e28780590c
出典データセット
uspto-grants-2011_01
特許番号
US07868187B2

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