Triethyl Phosphate → HCID 86740206, compound

HRID 371349Notes

Reaction equation

HRID 371349 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. After 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 1X8, 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. dissolutionAfter 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-d2cc135a88624dc6879cccb7868e67f9
Source dataset
uspto-grants-1985_07
Patent number
US04531001

Reaction notes

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