Trimethylphosphine → HCID 58460194, Verbindung

HRID 1946499

Reaktionsgleichung

Reaktionsgleichung von HRID 1946499
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14](O)[CH2:15][CH2:16][C:12]=3[N:11]=[C:10]2[CH:18]2[CH2:20][CH2:19]2)=[CH:4][CH:3]=1.[CH2:21]([O:23][C:24]([CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:25])[CH3:22].CP(C)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])([C:24]([O:23][CH2:21][CH3:22])=[O:25])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:15][CH2:16][C:12]=3[N:11]=[C:10]2[CH:18]2[CH2:20][CH2:19]2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 68983TrimethylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 80471Triethyl methanetricarboxylateHCID 584602013-[(4-Chlorophenyl)methyl]-2-cyclopropyl-3,4,5,6-tetrahydrocyclopenta[d]imidazol-4-ol

Produkt 1

HCID 58460194HCID 58460194, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of Intermediate 30 (95 mg) and triethylmethanetricarboxylate (0.140 ml) in toluene (1.5 ml) and tetrahydrofuran (1.5 ml), stirred at RT under an inert atmosphere of nitrogen, was added trimethylphosphine, 1M in toluene (0.658 ml). The resulting solution was cooled to −78° C. and diisopropyl azodicarboxylate (0.130 ml) was added dropwise via syringe and the reaction was stirred at −78° C. for 45 mins. The reaction mixture was removed from the cold bath and allowed to warm to RT and stirred under N2 atmosphere overnight. Reaction mixture concentrated in vacuo. The residue was taken up in DCM (20 ml) and washed with water (20 mL). The 2 phases were separated, the organic extract was dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (146 mg). LC/MS MH+503, Rt 3.37 min (5 minute run).

Aufarbeitung

  1. customThe reaction mixture was removed from the cold bath
  2. temperatureto warm to RT
  3. stirringstirred under N2 atmosphere overnight
  4. customReaction mixture
  5. concentrationconcentrated in vacuo
  6. washwashed with water (20 mL)
  7. customThe 2 phases were separated
  8. extractionthe organic extract
  9. customwas dried (hydrophobic frit)
  10. concentrationconcentrated under vacuum
  11. customThe residue was purified on silica using a cyclohexane
  12. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-059c371ffae94ed4b77ca596bcd02ca7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399444B2

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