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

HRID 1607338Notes

Reaction equation

HRID 1607338 reaction equation
[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

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl Chloride2×HCID 14797Potassium Hydroxide3×HCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6fafbd2859c24a9ba64522945df2dff8
Source dataset
uspto-grants-1989_09
Patent number
US04864021

Reaction notes

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