Acetic Anhydride → 5'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine

HRID 466090노트

반응식

HRID 466090 반응식
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH2:8]([O:15][C@@H:16]1[C@@H](CO)[O:19][C@@H:18]([N:23]2[CH:30]=[C:29]([F:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([O:15][C@@H:16]1[C@@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:19][C@@H:18]([N:23]2[CH:30]=[C:29]([F:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

생성물 1

HCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine수율 81.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A 3.33 ml quantity of acetic anhydride was added to a solution of 3.95 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 30 ml of pyridine, and the mixture was left to stand at 40° C overnight. The solvent was distilled off and the residue was dissolved in 30 ml of ethyl acetate. The solution was washed twice with 15 ml of water. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was placed on a silica gel column and eluted with chloroform, giving 3.62 g of the title compound in a yield of 81.5%.

후처리

  1. waitthe mixture was left
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in 30 ml of ethyl acetate
  4. washThe solution was washed twice with 15 ml of water
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washeluted with chloroform

출처 및 근거

ORD 기록
ord-ae968815880647bea357d818309643a7
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155113

반응 노트

불러오는 중…