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

HRID 2259170노트

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HRID 2259170 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91c99bf71296480490750b5424984162
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05472949

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