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

HRID 973792

反応式

HRID 973792 の反応式
[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]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 24408BromineHCID 55262Navuridine

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-37707a9b32a64b05be2a81c10c953f47
出典データセット
uspto-grants-1991_11
特許番号
US05064946

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