Pyridine → Fmoc-l-leucyl fluoride

HRID 7230

Reaktionsgleichung

Reaktionsgleichung von HRID 7230
[C:1]([NH:18][C@H:19]([C:24]([OH:26])=O)[CH2:20][CH:21]([CH3:23])[CH3:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:35]>C(#N)C>[C:1]([NH:18][C@H:19]([C:24]([F:35])=[O:26])[CH2:20][CH:21]([CH3:23])[CH3:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 1549133Fmoc-leucine

Produkt 1

HCID 11121802Fmoc-l-leucyl fluoride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

FMOC-L-Leucine (5 g, 14.14 mmol) (Bachem) was dissolved in acetonitrile (70 mL). Pyridine (1.14 mL, 14.14 mmol) (Aldrich) and cyanuric fluoride (1.91 g, 14.14 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (300 mL) was added and the resulting slurry was filtered. The filtrate was poured into a separatory funnel and the layers were separated. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford FMOC-L-leucyl fluoride as a white powder. (Yield 4.57 g, 91%).

Aufarbeitung

  1. filtrationthe resulting slurry was filtered
  2. additionThe filtrate was poured into a separatory funnel
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9c73895b2c0a498e9c55ac238f8665f2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084270B2

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