Carbon Dioxide → HCID 22808787, compound

HRID 905351Notes

Reaction equation

HRID 905351 reaction equation
C1(C)C(C([O:9][C@@H:10]2[C@@H:14]([CH2:15][O:16]C(C3C(C)=CC=CC=3)=O)[O:13][C@@H:12]([N:26]3[CH2:31][N:30]([CH2:32][CH2:33][CH2:34][CH3:35])[C:29](=[O:36])[NH:28][C:27]3=[O:37])[CH2:11]2)=O)=CC=CC=1.C[O-].[Na+].C(=O)=O.S(=O)(=O)(O)O>CO.C(Cl)(Cl)Cl.O>[C@@H:12]1([N:26]2[CH2:31][N:30]([CH2:32][CH2:33][CH2:34][CH3:35])[C:29](=[O:36])[NH:28][C:27]2=[O:37])[O:13][C@H:14]([CH2:15][OH:16])[C@@H:10]([OH:9])[CH2:11]1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 10942334Sodium MethoxideHCID 86736673HCID 86736673, compound

Product 1

HCID 22808787HCID 22808787, compoundYield 76.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent4×HCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

A reaction mixture consisting of 1.5 gm. (0.0287 mole) of 1-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-5-n-butyl-5,6-dihydro-s-triazine-2,4-(1H,3H)-dione (prepared in Part B, above), 70 ml. methanol, and 0.4 ml. of a solution of 25% sodium methoxide in methanol is stirred for 18 hours at 22° C. Thin-layer chromatography (25% methanol in chloroform) indicates one spot with a Rf 0.7. At this time solid carbon dioxide chips are added until the pH of the solution is 7.0. The methanol is removed by evaporation under reduced pressure. The residue thus obtained is dispersed in a mixture consisting of 50 ml. chloroform and 100 ml. water. The aqueous phase is washed five times with chloroform. The layers are separated, and the water is evaporated under reduced pressure at 40° C. There is obtained 0.97 gm. of residue. The residue is placed on a prepacked E. Merck Silica-gel-60 Column, Type C. The column is developed with a solvent mixture consisting of 10 percent methanol in chloroform at the rate of 3 ml. per minute. Fractions containing desired material, i.e. those fractions indicating positive char with a 50% aqueous sulfuric acid spray, are collected and the solvent mixture is removed by evaporation under reduced pressure. There is thus obtained 0.632 gm. (76.7 percent yield) of preparation of 1-(2-deoxy-β-D-ribofuranosyl)-5-n-butyl-5,6-dihydro-s-triazine-2,4-(1H,3H)-dione as a clear glass.

Workup

  1. customThe methanol is removed by evaporation under reduced pressure
  2. customThe residue thus obtained
  3. additionis dispersed in a mixture
  4. washThe aqueous phase is washed five times with chloroform
  5. customThe layers are separated
  6. customthe water is evaporated under reduced pressure at 40° C
  7. customThere is obtained 0.97 gm
  8. additionFractions containing desired material, i.e. those fractions
  9. customare collected
  10. customthe solvent mixture is removed by evaporation under reduced pressure
  11. custom(76.7 percent yield) of preparation of 1-(2-deoxy-β-D-ribofuranosyl)-5-n-butyl-5,6-dihydro-s-triazine-2,4-(1H,3H)-dione as a clear glass

Sources & evidence

ORD record
ord-368c45070fb248718b93c2c34cb32b26
Source dataset
uspto-grants-1983_12
Patent number
US04423212

Reaction notes

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