Benzoyl chloride → HCID 13715106, compound

HRID 466100Notes

Reaction equation

HRID 466100 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][O:16][C@@H:17]2[C@@H:21]([CH2:22][OH:23])[O:20][C@@H:19]([N:24]3[CH:31]=[C:30]([F:32])[C:28](=[O:29])[NH:27][C:25]3=[O:26])[CH2:18]2)=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:1]([N:27]1[C:28](=[O:29])[C:30]([F:32])=[CH:31][N:24]([C@@H:19]2[O:20][C@H:21]([CH2:22][O:23][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:17]([O:16][CH2:15][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:34][CH:33]=3)[CH2:18]2)[C:25]1=[O:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 10690564HCID 10690564, compound

Product 1

HCID 13715106HCID 13715106, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 0.23 ml quantity of benzoyl chloride was added to a solution of 0.25 g of 3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluorouridine in pyridine. The mixture was stirred at room temperature for 2 hours. The solvent was distilled off. To the residue were added ethyl acetate and water to separate the ethyl acetate layer. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was subjected to silica gel column chromatography using chloroform as an eluent, giving 0.27 g of the title compound in a yield of 70%.

Workup

  1. distillationThe solvent was distilled off
  2. additionTo the residue were added ethyl acetate and water
  3. customto separate the ethyl acetate layer
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a28511e277ca44df932c50780703c797
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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