3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 3'-O-benzyl-2'-deoxy-5-fluoro-5'-O-nicotinoyluridine

HRID 466087Notes

Reaction equation

HRID 466087 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH2:11]([O:18][C@@H:19]1[C@@H:23]([CH2:24][OH:25])[O:22][C@@H:21]([N:26]2[CH:33]=[C:32]([F:34])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH2:11]([O:18][C@@H:19]1[C@@H:23]([CH2:24][O:25][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=2)[O:22][C@@H:21]([N:26]2[CH:33]=[C:32]([F:34])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[CH2:20]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

Product 1

HCID 137150353'-O-benzyl-2'-deoxy-5-fluoro-5'-O-nicotinoyluridineYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 0.21 g quantity of nicotinoyl chloride hydrochloride was added to a solution of 0.20 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 10 ml of pyridine, and the mixture was left to stand at 80° C. for 3 hours. The solvent was distilled off and the residue was dissolved in 30 ml of ethyl acetate. The solution was washed twice with 20 ml of water. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was placed on a silica gel column and eluted with chloroform, giving 0.18 g of the title compound in a yield of 69%.

Workup

  1. waitthe mixture was left
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in 30 ml of ethyl acetate
  4. washThe solution was washed twice with 20 ml of water
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-0a03701523f84543a3e82660afabeb40
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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