Acetone → 2-(6-((2-Carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid

HRID 405133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405133
[O-][Mn](=O)(=O)=O.[K+].CC(C)=[O:9].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH:34]=[O:35])=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[O:25])=[N:22][CH:23]=2)[CH:17]=1>O>[C:29]([CH2:28][CH2:27][NH:26][C:24]([C:21]1[N:22]=[CH:23][C:18]([C:16]2[CH:17]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=2[C:34]([OH:35])=[O:9])=[CH:19][CH:20]=1)=[O:25])([OH:31])=[O:30]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Produkt 1

HCID 710599982-(6-((2-Carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Solid KMnO4 (460 mg, 2.9 mmol) was added to an acetone (14 mL) and water (5 mL) solution of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate, prepared as described in Example 6, (700 mg, 1.9 mmol) and the resulting mixture was heated to 50° C. After 20 h the resulting mixture was cooled, filtered through CELITE and washed with EtOAc. The aqueous phase was extracted with EtOAc and the combined extracts were washed with water and brine, dried (Na2SO4), and concentrated to yield the title compound, which was used in the next step without further purification.

Aufarbeitung

  1. customprepared
  2. temperatureAfter 20 h the resulting mixture was cooled
  3. filtrationfiltered through CELITE
  4. washwashed with EtOAc
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washthe combined extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3dc193234b77446b954ec90f6874eded
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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