Nicotinoyl chloride → 3'-O-benzyl-2'-deoxy-5-fluoro-5'-O-nicotinoyluridine

HRID 1607325Notes

Reaction equation

HRID 1607325 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10]([O:17][C@@H:18]1[C@@H:22]([CH2:23][OH:24])[O:21][C@@H:20]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:19]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH2:10]([O:17][C@@H:18]1[C@@H:22]([CH2:23][O:24][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)[O:21][C@@H:20]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:19]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 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 on 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 on anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-2cf4aa085b5743249e7d13c316f5662b
Source dataset
uspto-grants-1989_09
Patent number
US04864021

Reaction notes

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