Hydrochloric Acid → 4-Benzyl-4-hydroxy-2-hydroxyiminoglutaric acid

HRID 133667

반응식

HRID 133667 반응식
[OH-:1].[K+].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:15]([OH:23])(=[O:22])[CH2:16][C:17](C(O)=O)=O.Cl.[NH2:25]O.Cl>O.C1(C)C=CC=CC=1>[CH2:9]([C:10]([OH:14])([C:11]([OH:13])=[O:12])[CH2:17][C:16](=[N:25][OH:1])[C:15]([OH:23])=[O:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 970Oxaloacetic AcidHCID 997Phenylpyruvic acidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochloride

생성물 1

HCID 858482324-Benzyl-4-hydroxy-2-hydroxyiminoglutaric acid

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

After 16.23 g (having a purity of 85% by weight) of potassium hydroxide was dissolved in 45 ml of water, 5.0 g (30.5 mmol) of phenylpyruvic acid and 12.1 g (91.4 mmol) of oxalacetic acid were added to the resulting solution, for reaction at ambient temperature for 24 hours (about pH 13 at the start of the reaction). To the reaction solution was added 8.5 g (121.8 mmol) of hydroxylamine hydrochloride salt, for reaction at ambient temperature for 72 hours. The reaction solution was adjusted to pH 2.6, using 6N hydrochloric acid, and was then extracted in ethyl acetate. The organic layer was rinsed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated to dryness. The resulting residue was recrystallized in 20 ml of ethyl acetate and 80 ml of toluene, to obtain 4.0 g (15.1 mmol) of 4-benzyl-4-hydroxy-2-hydroxyiminoglutaric acid.

후처리

  1. customat the start of the reaction)
  2. customfor reaction at ambient temperature for 72 hours
  3. extractionwas then extracted in ethyl acetate
  4. washThe organic layer was rinsed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customThe resulting residue was recrystallized in 20 ml of ethyl acetate

출처 및 근거

ORD 기록
ord-96b8c3dba66e44f9880d074105ab17e0
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390909B2

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