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1-Methylimidazole → 5'-Deoxy-5-fluorocytidine

HRID 1089417
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HRID 1089417 반응식
C[N:2]1C=CN=C1.P(Cl)(Cl)(Cl)=O.C([O:20][C@@H:21]1[C@H:25]([O:26]C(=O)C2C=CC=CC=2)[C@@H:24]([CH3:35])[O:23][C@H:22]1[N:36]1[CH:43]=[C:42]([F:44])[C:40](=O)[NH:39][C:37]1=[O:38])(=O)C1C=CC=CC=1.[OH-].[NH4+]>C(#N)C>[F:44][C:42]1[C:40]([NH2:2])=[N:39][C:37](=[O:38])[N:36]([CH:43]=1)[C@@H:22]1[O:23][C@H:24]([CH3:35])[C@@H:25]([OH:26])[C@H:21]1[OH:20]
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참가 물질

6

반응물 4

HCID 13901-MethylimidazoleHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 121353572',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

생성물 1

HCID 100374995'-Deoxy-5-fluorocytidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of N-methylimidazole (0.8 ml) and phosphoryl chloride (0.28 ml) in acetonitrile (20 ml) was added 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine (500 mg) obtained above at 0° C. After stirring of the reaction mixture for 1.5 hours at room temperature 28% ammonium hydroxide (2.5 ml) was added to the mixture at 0° C., and the mixture was stirred for 1 hour at room temperature. Acetonitrile and ammonia were removed under reduced pressure. The residue was acidified with 1N-HCl and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give 155 mg of 2',3'-di-O-benxoyl- 5'-deoxy-5-fluorocytidine, mp 192°~194° C.; MS 476 ((M+Na)+).

후처리

  1. customobtained above at 0° C
  2. additionwas added to the mixture at 0° C.
  3. customAcetonitrile and ammonia were removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-26fa1d2236fd4819a2298b048de21c8d
출처 데이터셋
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04966891

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