Water → HCID 18633450, compound

HRID 232350Notes

Reaction equation

HRID 232350 reaction equation
[CH2:1]([C:3]1[C:4](=[O:37])[NH:5][C:6](=[O:36])[N:7]([CH:35]=1)[C@@H:8]1[O:34][C@H:12]([CH2:13][O:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[OH-].[K+].[CH2:40](Cl)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O>C1C=CC=CC=1.O1CCOCC1.C(O)(=O)C>[CH2:40]([O:11][C@@H:10]1[C@@H:12]([CH2:13][O:14][C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:34][C@@H:8]([N:7]2[CH:35]=[C:3]([CH2:1][CH3:2])[C:4](=[O:37])[NH:5][C:6]2=[O:36])[CH2:9]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 13062021HCID 13062021, compound

Product 1

HCID 18633450HCID 18633450, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6.5 g of 2'-deoxy-5-ethyl-5'-O-trityluridine, 19 g of powdered potassium hydroxide and 9.5 ml of benzyl chloride in a mixture of 60 ml of benzene and 21 ml of dioxane was stirred and heated under reflux for 4 hours. After cooling 65 ml of water and 20 ml of acetic acid were added and the phases were separated. The organic phase was washed twice with 90 ml of water each time, dried over anhydrous sodium sulfate and evaporated to give 4.5 g of 3'-O-benzyl-2'-deoxy-5-ethyl-5'-O-trityluridine in the form of a sticky solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. additionwere added
  4. customthe phases were separated
  5. washThe organic phase was washed twice with 90 ml of water each time
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7f497070b3a14a54a5dcd189792f3e70
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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