Pyridine → Carbamic acid, (2-fluoro-2-oxoethyl)-, 9H-fluoren-9-ylmethyl ester

HRID 7227

Reaktionsgleichung

Reaktionsgleichung von HRID 7227
[C:1]([NH:18][CH2:19][C:20]([OH:22])=O)([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:31]>ClCCl>[C:1]([NH:18][CH2:19][C:20]([F:31])=[O: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 93124Fmoc-Gly-OH

Produkt 1

HCID 11011991Carbamic acid, (2-fluoro-2-oxoethyl)-, 9H-fluoren-9-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

FMOC-Glycine (5.02 g, 16.82 mmol) (Bachem) was dissolved in dichloromethane (85 mL). Pyridine (1.36 mL, 16.82 mmol) (Aldrich) and cyanuric fluoride (2.27 g, 16.82 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 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-glycyl fluoride as a white powder. (Yield 3.67 g, 73%).

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-8e925202aa5c48a68b53aa693faeea25
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084270B2

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