4-Toluenesulfonyl chloride → HCID 5280128, compound

HRID 232368Notes

Reaction equation

HRID 232368 reaction equation
[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][O:14][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[C@@H:10]([OH:11])[CH2:9]1)[CH3:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66377Edoxudin

Product 1

HCID 5280128HCID 5280128, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

26 g of 2'-deoxy-5-ethyluridine were dissolved in 400 ml of dry pyridine. The solution was cooled to 0° C. and stirred while 20 g of p-toluenesulfonyl chloride were added portionwise. Stirring at 0° C. was continued for 1 hour and the mixture was then left to stand at 4° C. overnight. The solvent was removed by evaporation and the residue was re-evaporated with toluene. The residue was shaken with 200 ml of methanol and left to stand in a refrigerator for 2.5 hours to give a solid which was removed by filtration, washed with methanol and dried in vacuo to give 18 g of crude product of melting point 183° C. (decomposition). Recrystallization from 450 ml of ethanol gave 13 g of pure 2'-deoxy-5-ethyl-5'-O-(p-toluenesulfonyl)uridine of melting point 189°-190° C. (decomposition).

Workup

  1. additionwere added portionwise
  2. waitthe mixture was then left
  3. waitto stand at 4° C. overnight
  4. customThe solvent was removed by evaporation
  5. customthe residue was re-evaporated with toluene
  6. stirringThe residue was shaken with 200 ml of methanol
  7. waitleft
  8. waitto stand in a refrigerator for 2.5 hours
  9. customto give a solid which
  10. customwas removed by filtration
  11. washwashed with methanol
  12. customdried in vacuo
  13. customto give 18 g of crude product of melting point 183° C. (decomposition)
  14. customRecrystallization from 450 ml of ethanol

Sources & evidence

ORD record
ord-defebcd73e7d4fd1b7058d6949b9f7c0
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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