Acetic Anhydride → 3'-Azido-2',3'-dideoxy-5-bromouridine

HRID 973792

Reaktionsgleichung

Reaktionsgleichung von HRID 973792
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].C(OC(=O)C)(=O)C.[Br:26]Br>C(O)(=O)C>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[C:17]([Br:26])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 24408BromineHCID 55262Navuridine

Produkt 1

HCID 649783'-Azido-2',3'-dideoxy-5-bromouridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

3'-Azido-5-bromo-2',3'-dideoxyuridine was prepared from the known 3'-azido-2',3'-dideoxyuridine (T. A. Krenitsky, et al., J. Med. Chem., 26, 891, (1983)) (0.827 g, 3.3 mMol) by first acetylating the 5'-hydroxyl group with acetic anhydride (15 mL) then by brominating the 5 position by the addition of acetic acid (0.5 mL) and bromine (0.566 g). The red-brown solution was stirred at room temperature for two hours. The reaction was taken to an oil in vacuo and triturated with ethyl ether. The oil was dissolved in methanol ammonia to remove the acetyl group. The desired product was isolated by chromatography on silica gel by elution with CHCl3 :MeOH (95:5 v/v). The yield was 32%; mp=148°-149° C.

Aufarbeitung

  1. customtriturated with ethyl ether
  2. dissolutionThe oil was dissolved in methanol ammonia
  3. customto remove the acetyl group

Quellen und Nachweise

ORD-Eintrag
ord-37707a9b32a64b05be2a81c10c953f47
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05064946

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