Carbon Dioxide → HCID 22808787, compound

Participants

Reaction Steps

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.

Provenance & Evidence