Triethyl Phosphate → HCID 86740206, compound

HRID 1981926Notes

Reaction equation

HRID 1981926 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[C:13]1[Se:14][CH:15]=[C:16]([C:18]([NH2:20])=[O:19])[N:17]=1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O.C([O:28][P:29](OCC)([O:31]CC)=[O:30])C.[OH-].[Na+]>>[C:1]([O:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][O:12][P:29]([OH:31])([OH:30])=[O:28])[O:7][C@H:6]1[C:13]1[Se:14][CH:15]=[C:16]([C:18]([NH2:20])=[O:19])[N:17]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 6535Triethyl PhosphateHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 86740207HCID 86740207, compound

Product 1

HCID 86740206HCID 86740206, compound

Procedure

2-(2-O-Acetyl-β-D-ribofuranosyl)selenazole-4-carboxamide is treated with 1 to 5 equivalents of phosphoryl chloride in the presence of triethylphosphate at 0 degrees C. Afer complete dissolution is obtained, the solution is poured over crushed ice and adjusted with sodium hydroxide solution to pH 7, extracted with chloroform, and placed on a column of ion exchange resin (Dowex AG 1×8, formate). The column is first washed with water, then the product is eluted with a gradient of water-formic acid. The fractions containing pure product are pooled and evaporated to dryness. The residue is recrystallized from ethanol-water to provide the free acid of the title compound as a crystalline solid.

Workup

  1. dissolutionAfer complete dissolution
  2. customis obtained
  3. additionthe solution is poured
  4. customover crushed ice
  5. extractionextracted with chloroform
  6. washThe column is first washed with water
  7. washthe product is eluted with a gradient of water-formic acid
  8. additionThe fractions containing pure product
  9. customevaporated to dryness
  10. customThe residue is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-0c434cc19c5e4be2b2eea730265486d1
Source dataset
uspto-grants-1986_06
Patent number
US04594414

Reaction notes

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