Dicyclohexylcarbodiimide → 4-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)propanoate

HRID 1879075

Reaktionsgleichung

Reaktionsgleichung von HRID 1879075
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:44]1[CH:52]=[CH:51][C:47]([C:48]([NH2:50])=[O:49])=[CH:46][CH:45]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][C:11]2[C:6](=[CH:5][CH:4]=[C:3]([CH:2]([CH3:1])[C:15]([O:17][C:44]3[CH:52]=[CH:51][C:47]([C:48](=[O:49])[NH2:50])=[CH:46][CH:45]=3)=[O:16])[CH:12]=2)[CH:7]=1

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 650524-HydroxybenzamideHCID 156391NaproxenHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 593455934-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)propanoateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 1 (naproxen, 4 g, 17.4 mmol) in 80 mL of dimethylformamide, hydroxybenzotriazole (2.59 g, 19.14 mmol) and DCC (2.59 g, 19.14 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (4, 3.58 g, 26.1 mmol) was added and stirred for 1 h at 0° C. and 2 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10% and than dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 5 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate (5) was obtained (1.91 g, 32% yield).

Aufarbeitung

  1. stirringstirred for 1 h at 0° C. and 2 h at room temperature
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe oily residue thus obtained
  6. washthe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
  7. dry with materialthan dried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate (5)
  11. customwas obtained (1.91 g, 32% yield)

Quellen und Nachweise

ORD-Eintrag
ord-ef822906597349e5960ff0f0a902b774
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314140B2

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