Acetic Anhydride → HCID 12896718, compound

HRID 2361627Notes

Reaction equation

HRID 2361627 reaction equation
[C@@H:1]1([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]2=[O:17])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].C(O[C:22](=[O:24])[CH3:23])(=O)C>N1C=CC=CC=1>[C:2]([O:3][C@H:2]1[C@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@@H:6]([CH2:8][O:9][C:22](=[O:24])[CH3:23])[O:7][C@H:1]1[N:10]1[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]1=[O:17])(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18323Uracil Arabinoside

Product 1

HCID 12896718HCID 12896718, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

500 mg (2.05 mmol) of the above product 3 is taken as the starting material, and dissolved in 35 mL of pyridine. Then 11 ml of acetic anhydride is added with continuously stirring. The solution is concentrated under reduced pressure by removing the residual part of the solution after the completion of the reaction, and then purified by rapid column chromatography (acetone/n-hexane=4:5). A white product (1-(2′,3′,5′-Tri-O-acetyl-β-D-arabinofuranosyl)-pyrimidin-2,4-(3H)-dione) 4 is obtained. Its weight and yield are 675 mg and 89% respectively.

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. customby removing the residual part of the solution
  3. customafter the completion of the reaction
  4. custompurified by rapid column chromatography (acetone/n-hexane=4:5)

Sources & evidence

ORD record
ord-19a103e640fc4e2f93ba7714bc8c86ab
Source dataset
uspto-grants-2014_04
Patent number
US08691789B2

Reaction notes

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