Water → 5-amino-4-cyano-1-(2,3,5-tri-O-propionyl-beta-D-ribofuranosyl)imidazole

Participants

Reaction Steps

A solution of 840 g of 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide, 5.4 l of dichloromethane and 1.38 l of triethylamine was cooled to 0° C. or less, and a solution of 196 ml of phosphorus oxychloride in dichloromethane (1.8 l) was added dropwise thereto while maintaining the temperature below 0° C. After stirring for 1.5 hours, 2 l of water was added to the mixture below 0° C. and the dichloromethane layer was separated. The dichloromethane layer was washed successively with 2 l each of water, twice with 2 l of 1 N hydrochloric acid, and twice with 2 l each of a saturated aqueous sodium chloride solution, and then concentrated to dryness under reduced pressure to obtain 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carbonitrile as a yellow brown viscous syrup.

Provenance & Evidence