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

HRID 973792

반응식

HRID 973792 반응식
[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]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 24408BromineHCID 55262Navuridine

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-37707a9b32a64b05be2a81c10c953f47
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064946

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