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

HRID 466090ノート

反応式

HRID 466090 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-ae968815880647bea357d818309643a7
出典データセット
uspto-grants-1992_10
特許番号
US05155113

反応ノート

読み込み中…