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

HRID 973792

Reaction equation

HRID 973792 reaction equation
[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]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24408BromineHCID 55262Navuridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-37707a9b32a64b05be2a81c10c953f47
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Linked notes

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