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

HRID 1089416

반응식

HRID 1089416 반응식
[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

참가 물질

4

반응물 2

HCID 7412Benzoyl chlorideHCID 18343Doxifluridine

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-dbb8ebe7c93d44c590af8e150c619808
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04966891

연결된 노트

불러오는 중…