Benzoyl chloride → 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

HRID 1089416

反応式

HRID 1089416 の反応式
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:12]([CH3:13])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:18]([O:9][C@@H:8]1[C@H:10]([O:11][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:12]([CH3:13])[O:14][C@H:7]1[N:6]1[CH:15]=[C:2]([F:1])[C:3](=[O:17])[NH:4][C:5]1=[O:16])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 18343Doxifluridine

生成物 1

HCID 121353572',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a stirred solution of 5'-deoxy-5-fluorouridine (24.6 g) in dry pyridine (150 ml) was added dropwise 24.5 ml of benzoyl chloride over 10 minutes at 0° C. and the mixture was stirred for 5 hours at room temperature. After removal of pyridine under reduced pressure the residue was partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate - n-hexane to give 38.9 g of 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine, MS 455 (MH+).

後処理

  1. customAfter removal of pyridine under reduced pressure the residue
  2. customwas partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate - n-hexane

出典と根拠

ORDレコード
ord-dbb8ebe7c93d44c590af8e150c619808
出典データセット
uspto-grants-1990_10
特許番号
US04966891

関連ノート

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