Benzoyl chloride → 5'-O-acetyl-3'-O-benzyl-3-benzoyl-2'-deoxy-5-fluorouridine

HRID 466089ノート

反応式

HRID 466089 の反応式
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>O1CCOCC1>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[N:14]([C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine

生成物 1

HCID 137150635'-O-acetyl-3'-O-benzyl-3-benzoyl-2'-deoxy-5-fluorouridine収率 78.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 0.20 g of 5'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine in 10 ml of dioxane were added 0.29 g of benzoyl chloride and 0.73 ml of triethylamine, and the mixture was left to stand at 80° C. for 2 hours. The solvent was distilled off and the residue was dissolved in 50 ml of ethyl acetate. The solution was washed with 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 0.2 g of the title compound as an oil in a yield of 78%.

後処理

  1. waitthe mixture was left
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  4. washThe solution was washed with 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-6c3152b55b2a45d389f0975f24c7387d
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…