Pyridine → Fmoc-l-tryptophanyl fluoride

HRID 7233

Reaktionsgleichung

Reaktionsgleichung von HRID 7233
[C:1]([NH:18][C@H:19]([C:30]([OH:32])=O)[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)([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:41]>ClCCl>[C:1]([NH:18][C@H:19]([C:30]([F:41])=[O:32])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)([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 978343Fmoc-L-tryptophan

Produkt 1

HCID 11362381Fmoc-l-tryptophanyl fluoride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

FMOC-L-Tryptophan (5 g, 11.72 mmol) (Bachem) was dissolved in dichloromethane (60 mL). Pyridine (0.95 mL, 11.72 mmol) (Aldrich) and cyanuric fluoride (1.58 g, 11.72 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 6.5 hours. 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-L-tryptophanyl fluoride as a beige powder. (Yield 4.36 g, 87%).

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-0c4289f38f9b4359b0462549c3b30f31
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084270B2

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