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

HRID 1089417
ノート
印刷プレビュー

反応式

HRID 1089417 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

HCID 100374995'-Deoxy-5-fluorocytidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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)+).

後処理

  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

出典と根拠

ORDレコード
ord-26fa1d2236fd4819a2298b048de21c8d
出典データセット
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04966891

反応ノート

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