6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine → Fludarabine

HRID 1646667

Reaktionsgleichung

Reaktionsgleichung von HRID 1646667
[N:1]([C:4]1[N:12]=[C:11]([F:13])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:14]1[O:34][C@H:33]([CH2:35][O:36]CC2C=CC=CC=2)[C@@H:24]([O:25]CC2C=CC=CC=2)[C@@H:15]1[O:16]CC1C=CC=CC=1)=[N+]=[N-]>COCCO.[Pd](Cl)Cl>[C@@H:14]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:11]([F:13])=[N:12][C:4]=3[NH2:1])[O:34][C@H:33]([CH2:35][OH:36])[C@@H:24]([OH:25])[C@@H:15]1[OH:16]

Komponenten

4

Edukt 1

HCID 544897616-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine

Produkt 1

HCID 657237FludarabineAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 80192-MethoxyethanolLösungsmittel

Versuchsvorschrift

6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine (0.19 g) was dissolved in 2-methoxyethanol (20 mL) with palladium (II) chloride (PdCl2) (20 mg) and activated carbon and the mixture was hydrogenated at 55 pounds per square inch (psi) in a Parr shaker. The reaction was monitored by thin layer chromatography (TLC) until complete. The mixture was then filtered through celite and the filtrate was concentrated in vacuo. Three times, the residue was dissolved in ethanol and reconcentrated. Then the residue was recrystalized from ethanol/water to obtain 0.063 g of the title compound which was consistent in its structure with an authentic sample by IR and TLC.

Aufarbeitung

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThree times, the residue was dissolved in ethanol
  4. customThen the residue was recrystalized from ethanol/water

Quellen und Nachweise

ORD-Eintrag
ord-4d0b759483994145a1322818e9484f05
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180824

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