Hydrochloric Acid → 4-Hydroxy-4-(4-hydroxyphenylmethyl)-2-hydroxyiminoglutaric acid

HRID 252667

反応式

HRID 252667 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:14]([OH:22])(=[O:21])[CH2:15][C:16](C(O)=O)=O.Cl.[NH2:24][OH:25].Cl>[OH-].[K+].O>[OH:13][C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)([C:10]([OH:12])=[O:11])[CH2:16][C:15](=[N:24][OH:25])[C:14]([OH:22])=[O:21]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 970Oxaloacetic AcidHCID 9794-Hydroxyphenylpyruvic AcidHCID 443297Hydroxyamine hydrochloride

生成物 1

HCID 865958174-Hydroxy-4-(4-hydroxyphenylmethyl)-2-hydroxyiminoglutaric acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 14797Potassium Hydroxide溶媒

実験手順

To 10 ml of water in which were dissolved 3.18 g of potassium hydroxide, were added 1.0 g (5.55 mmol) of 4-hydroxyphenylpyruvic acid and 2.2 g (16.7 mmol) of oxalacetic acid, for reaction at ambient temperature for 72 hours (about pH 13 at the start of the reaction). Hydroxylamine hydrochloride salt of 1.54 g (22.2 mmol) was added to the reaction solution, for reaction at ambient temperature for 10 hours. The reaction solution was then adjusted to pH 2.6, using 6N hydrochloric acid, for extraction using ethyl acetate. The organic layer was rinsed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated to dryness, to obtain 0.7 g (2.47 mmol) of 4-hydroxy-4-(4-hydroxyphenylmethyl)-2-hydroxyiminoglutaric acid as a crude product. Further, the crude product was recrystallized in methanol and toluene, to obtain 0.22 g (0.78 mmol) of 4-hydroxy-4-(4-hydroxyphenylmethyl)-2-hydroxyiminoglutaric acid in crystal.

後処理

  1. customfor reaction at ambient temperature for 72 hours (about pH 13
  2. customat the start of the reaction)
  3. extractionfor extraction
  4. washThe organic layer was rinsed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-0c47d330346b41c1b63d1c889d55f041
出典データセット
uspto-grants-2011_01
特許番号
US07868187B2

関連ノート

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