Water → HCID 178440173, Verbindung

HRID 248623

Reaktionsgleichung

Reaktionsgleichung von HRID 248623
[O:1]=[C:2]([C:7]1[N:8]([C:12]2[N:13]=[C:14]([CH2:38][CH2:39][CH3:40])[N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:16]=2[C:17]([O-:19])=[O:18])[CH:9]=[CH:10][CH:11]=1)[C:3]([F:6])([F:5])[F:4].O.C(=O)([O-])[O-].[K+].[K+].SCC(CO)O>CN(C=O)C>[O:1]=[C:2]([C:7]1[N:8]([C:12]2[N:13]=[C:14]([CH2:38][CH2:39][CH3:40])[N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:16]=2[C:17]([OH:19])=[O:18])[CH:9]=[CH:10][CH:11]=1)[C:3]([F:4])([F:5])[F:6]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 7291ThioglycerolHCID 11430Potassium Carbonate2×HCID 178440172HCID 178440172, Verbindung

Produkt 1

HCID 178440173HCID 178440173, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-[2-(1-Oxo-2,2,2-trifluoroethyl)-1H-pyrrol-1-yl]-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylate (2.5 g) from Example 13 was dissolved in DMF (45 mL). Water (0.4 mL) followed by potassium carbonate (3.1 g) were added and the reaction mixture stirred at room temperature for 48 hours. Tlc of the reaction mixture showed the reaction to be incomplete. Additional potassium carbonate (0.6 g) and water (0.2 mL) were added and the reaction mixture stirred at room temperature for an another 18 hours. The insoluble materials were removed from the reaction mixture by filtration and washed with DMF A 10% citric acid solution (100 mL) was added slowly to the filtrate and the resulting mixture extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent removed under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to afford 2.06 g (85% yield) of the title compound, mp 185°-188° C., MS (FAB, thioglycerol) 550.3 (M+1).

Aufarbeitung

  1. additionwere added
  2. customthe reaction
  3. stirringthe reaction mixture stirred at room temperature for an another 18 hours
  4. customThe insoluble materials were removed from the reaction mixture by filtration
  5. washwashed with DMF A 10% citric acid solution (100 mL)
  6. additionwas added slowly to the filtrate
  7. extractionthe resulting mixture extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent removed under reduced pressure
  11. customThe residue was recrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a94c4ec8e2df434896c25474238912c6
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210211

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