Dimethylformamide → HCID 86623053, Verbindung

HRID 1360001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360001
CN(C=[O:5])C.[C:6]([CH:13]([NH2:16])[CH2:14]Br)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:17]1[CH:18]=[CH:19][C:20]([NH:27][C:28]2[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=2[Cl:34])=[C:21]([CH2:23][C:24]([O-:26])=[O:25])[CH:22]=1.[Na+]>C(OCC)(=O)C>[C:6]([C:13]([NH2:16])([OH:5])[CH3:14])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:17]1[CH:18]=[CH:19][C:20]([NH:27][C:28]2[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:35])=[C:21]([CH2:23][C:24]([OH:26])=[O:25])[CH:22]=1

Komponenten

5

Edukt 3

HCID 6228Dimethylformamide2×HCID 5018304Diclofenac sodiumHCID 22273677HCID 22273677, Verbindung

Produkt 1

HCID 86623053HCID 86623053, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After ice-cooling 5 ml of DMF solution containing 2.287 g (10.2 mmol) of the Boc-aminoethyl bromide obtained in Reference Example 5, 6 ml of DMF solution containing 3.255 g (10.2 mmol) of diclofenac sodium was added thereto, followed by stirring at room temperature overnight. The mixture was stirred at 60° C. for 11 hours and then stirred at room temperature overnight. Ethyl acetate was added thereto, and separation by washing with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine consecutively was carried. After dehydration with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=20:1, 0.5% triethylamine) to give 2.675 g (60%) of the titled compound. The structure was identified by 1H-NMR.

Aufarbeitung

  1. additionwas added
  2. stirringThe mixture was stirred at 60° C. for 11 hours
  3. stirringstirred at room temperature overnight
  4. customseparation
  5. washby washing with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine
  6. customAfter dehydration with sodium sulfate, ethyl acetate was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=20:1, 0.5% triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-0ca8b489f42c4f0d8791a974c036f2db
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879817B2

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