4'-Hydroxyacetophenone → HCID 69081870, Verbindung

HRID 1724721

Reaktionsgleichung

Reaktionsgleichung von HRID 1724721
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:15])=[O:14])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.O[C:43]1[CH:48]=[CH:47][C:46]([C:49](=[O:51])[CH3:50])=[CH:45][CH:44]=1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([O:15][C:43]2[CH:48]=[CH:47][C:46]([C:49](=[O:51])[CH3:50])=[CH:45][CH:44]=2)=[O:14])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 74694'-HydroxyacetophenoneHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 6932185(R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

Produkt 1

HCID 69081870HCID 69081870, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

At 0° C., 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylic acid (1.0 g) is dissolved in ethyl acetate (25 ml), dicyclohexylcarbodiimide (DCC; 1.26 g) is then added and the reaction mixture is subjected to agitation for 45 minutes at 0° C. Dimethylaminopyridine (DMAP; 100 mg) and 4′-hydroxyacetophenone (565 mg) are successively added, the reaction mixture is then left to return to room temperature. After 5 hours of agitation, the mixture is filtered and the filtrate is washed with a sodium hydrogen carbonate saturated solution, then with a sodium chloride saturated solution. The organic phase is dried on MgSO4, filtered and concentrated. The obtained orange oil is purified by chromatography on silica to obtain the desired product as a transparent oil (940 mg).

Aufarbeitung

  1. waitthe reaction mixture is then left
  2. customto return to room temperature
  3. waitAfter 5 hours of agitation
  4. filtrationthe mixture is filtered
  5. washthe filtrate is washed with a sodium hydrogen carbonate saturated solution
  6. customThe organic phase is dried on MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe obtained orange oil is purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-f7a900afe54647e698a35ba0b75d4dfd
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488755B2

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