Sodium Iodide → 2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine

HRID 466103

반응식

HRID 466103 반응식
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:36])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37](Cl)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[K+].[I-].[Na+]>O1CCOCC1.O.C(O)(=O)C>[CH2:37]([O:36][C@@H:23]1[C@@H:22]([CH2:21][O:20][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 7503Benzyl Chloride2회HCID 14797Potassium Hydroxide3회HCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

생성물 1

HCID 106747232'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine수율 70.6%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
40 °C

실험 절차

A 10 g quantity of 2'-deoxy-5'-O-trityl-5-fluorouridine was dissolved in 100 ml of dioxane. To the solution were added 2.9 ml of benzyl chloride, 6.9 g of particles of potassium hydroxide and 3.56 g of sodium iodide. The mixture was stirred at 40° C. for 4 hours, and 2.9 ml of benzyl chloride and 1.15 g of potassium hydroxide were added and stirred for 1 hour. Thereto was added water to dissolve the potassium hydroxide in water. The solution was adjusted to a pH of about 3 with acetic acid and extracted with ethylene dichloride. The extract was washed with water and the ethylene dichloride layer was dried over anhydrous sodium sulfate. The sodium sulfate was separated by filtration and the solvent was distilled off, giving 8 g of 2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine as an oil.

후처리

  1. stirringstirred for 1 hour
  2. extractionextracted with ethylene dichloride
  3. washThe extract was washed with water
  4. dry with materialthe ethylene dichloride layer was dried over anhydrous sodium sulfate
  5. customThe sodium sulfate was separated by filtration
  6. distillationthe solvent was distilled off

출처 및 근거

ORD 기록
ord-a32d777dd9ca42ef9ca0c896fd643e53
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155113

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