Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylmethyl)- → Navuridine

HRID 892420

Reaktionsgleichung

Reaktionsgleichung von HRID 892420
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:7][C@@H:6]([N:30]2[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:5]1)=[N+:2]=[N-:3]>C(O)(=O)C>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:30]2[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:5]1)=[N+:2]=[N-:3]

Komponenten

3

Edukt 1

HCID 13711964Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylmethyl)-

Produkt 1

HCID 55262NavuridineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3'-azido-5'-O-trityl-2',3'-dideoxyuridine (63 g, 0.132 mol) and 300 ml of acetic acid (80%) was heated at 95°-100° C. for two hours. The reaction mixture was cooled in an ice-bath and the solid separated was filtered off. The filtrate was evaporated to dryness. The residue was dissolved in a methanol-chloroform mixture and concentrated to a syrup. The purification of the residue by flash vacuum chromatography over a silica gel column eluting sequentially with chloroform-methanol (70:1), chloroform-methanol (50:1) and finally chloroform-methanol (30:1), yielding 23 g (70%) of 3'-azido-2',3'-dideoxyuridine.

Aufarbeitung

  1. temperaturewas heated at 95°-100° C. for two hours
  2. temperatureThe reaction mixture was cooled in an ice-bath
  3. customthe solid separated
  4. filtrationwas filtered off
  5. customThe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved in a methanol-chloroform mixture
  7. concentrationconcentrated to a syrup
  8. customThe purification of the residue by flash vacuum chromatography over a silica gel column
  9. washeluting sequentially with chloroform-methanol (70:1), chloroform-methanol (50:1) and finally chloroform-methanol (30:1)

Quellen und Nachweise

ORD-Eintrag
ord-7b8b7c1892f84008934e1fe7c64ed1aa
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118672

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