Ammonia → HCID 53660528, compound

Participants

Reaction Steps

1.9 g (4.4 mmoles) of 1-hydrazino-2,3,5-tri-O-benzyl-D-ribose are dissolved in 10 ml of absolute methanol. To the solution 0.54 g (4.4 mmoles) of ethoxymethylenemalonodinitrile, dissolved in 10 ml of absolute methanol, are added dropwise. Slight heating occurs. Stirring is carried out at room temperature for 24 hours and following this for completion of the reaction refluxing is carried out for 30 minutes. Following this the product is separated by column chromatography. As an eluting agent use is made of a mixture of benzene and acetone (85:15). Rf = 0.61. A yellow oil is obtained which is boiled with 7 ml of orthoformic acid triethylester for 3 hours under reflux. (Bath temperature 160° C.)(3). After removal of the remaining ortho-ester the oil obtained is dissolved in 13 ml of ethanol. NH3 is introduced into the solution at room temperature (for four hours). After removal of the ethanol purification is carried out by column chromatography (benzene to acetone = 50 to 50). Rf = 0.58. A yellow oil is obtained. Yield: 1.36 g (52 %).

Provenance & Evidence