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

HRID 252667

반응식

HRID 252667 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 14797Potassium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c47d330346b41c1b63d1c889d55f041
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868187B2

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