Sodium Chloride → 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine

HRID 2259170ノート

反応式

HRID 2259170 の反応式
[I-].[Na+].Cl[Si](C)(C)C.[Cl-].[Na+].C(O[C@@H:14]1[O:26][C@H:25]([CH3:27])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]1[O:16][C:17](=[O:19])[CH3:18])(=O)C.[F:28][C:29]1[C:30]([NH2:36])=[N:31][C:32](=[O:35])[NH:33][CH:34]=1>C(#N)C>[C:17]([O:16][C@@H:15]1[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:25]([CH3:27])[O:26][C@H:14]1[N:33]1[CH:34]=[C:29]([F:28])[C:30]([NH2:36])=[N:31][C:32]1=[O:35])(=[O:19])[CH3:18]

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 11821332beta-D-Ribofuranose, 5-deoxy-, 1,2,3-triacetateHCID 178509021HCID 178509021、化合物

生成物 1

HCID 118096352',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine収率 49%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of sodium iodide (3.6 g) and chlorotrimethylsilane (794 ml) in dry acetonitrile (15 ml) was stirred with molecular sieves 4A (200 mg) at 0° C. for 5 minutes (colorless sodium chloride deposited during stirring). 1,2,3-Tri-O-acetyl-5-deoxy-β-D-ribofuranose (2.0 g) was added and the mixture was stirred at 0° C. for 30 min. Then, a solution of the trimethylsilylated 5-fluorocytosine, freshly prepared from 5-fluorocytosine (1.12 g), in dry acetonitrile (5 ml) was added at 0° C. and stirring was continued for 3 h at room temperature. The mixture was filtered, the filtrate was concentrated in vacuo, and the residue was partitioned between dichloromethane and saturated aq. sodium bicarbonate solution. The aqueous layer was extracted with CH2Cl2 /MeOH (10:1). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography using CH2Cl2 /MeOH (15:1) as an eluent, followed by recrystallization from isopropanol to give 1.24 g of 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine.

後処理

  1. additionwas added at 0° C.
  2. stirringstirring
  3. waitwas continued for 3 h at room temperature
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was partitioned between dichloromethane and saturated aq. sodium bicarbonate solution
  7. extractionThe aqueous layer was extracted with CH2Cl2 /MeOH (10:1)
  8. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by silica gel chromatography
  11. customfollowed by recrystallization from isopropanol

出典と根拠

ORDレコード
ord-91c99bf71296480490750b5424984162
出典データセット
uspto-grants-1995_12
特許番号
US05472949

反応ノート

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