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Permanganate → (S)-2(isopropylsulfonyl)-amino-3-methyl-butyric acid-N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide

HRID 2389
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2389
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:25])[C@@:15]([NH2:24])([S:19]([CH:21]([CH3:23])[CH3:22])=[O:20])[CH:16]([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Mn]([O-])(=O)(=O)=[O:27].[K+].[Mn]([O-])(=O)(=O)=O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:25])[C@@:15]([NH2:24])([S:19]([CH:21]([CH3:23])[CH3:22])(=[O:27])=[O:20])[CH:16]([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24401PermanganateHCID 516875Potassium PermanganateHCID 67569267(S)-2-(isopropylsulfinyl)-amino-3-methyl-butyric acid N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide

Produkt 1

HCID 67569348(S)-2(isopropylsulfonyl)-amino-3-methyl-butyric acid-N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel
2×

Versuchsvorschrift

3.7 g of (S)-2-(isopropylsulfinyl)-amino-3-methyl-butyric acid N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide (Example 3.90) are dissolved in 50 ml of acetone at room temperature. An acetone solution saturated with potassium permanganate is added dropwise to this stirred solution until the reaction mixture retains the violet colour of the permanganate; the reaction mixture is then stirred at room temperature for 45 minutes. The resulting manganese dioxide is removed by filtration over Celite. The filtrate is evaporated to dryness and the resulting residue is dissolved in 500 ml of methyl acetate. This organic phase is washed once with 200 ml of water, dried over sodium sulfate and concentrated. The resulting residue is chromatographed over silica gel with a mixture of one part of methyl acetate and one part of n-hexane. (S)-2-(isopropylsulfonyl)-amino-3-methyl-butyric acid N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide, which can be further purified by recrystallization from methyl acetate/n-hexane, is obtained, melting point 86°-87° C.

Aufarbeitung

  1. customThe resulting manganese dioxide is removed by filtration over Celite
  2. customThe filtrate is evaporated to dryness
  3. dissolutionthe resulting residue is dissolved in 500 ml of methyl acetate
  4. washThis organic phase is washed once with 200 ml of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is chromatographed over silica gel with a mixture of one part of methyl acetate and one part of n-hexane
  8. custom(S)-2-(isopropylsulfonyl)-amino-3-methyl-butyric acid N-[2-(3,4-dimethoxyphenyl)-ethyl]-amide, which can be further purified by recrystallization from methyl acetate/n-hexane
  9. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-4b5f4cb68ad14383914fad9f4aa70cd0
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728875

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