Реакция #934945

Уравнение реакции

water

5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide

triethylamine

phosphorus oxychloride

→

5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carbonitrile

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураwhile maintaining the temperature below 0° C
2. 2
   Другоеthe dichloromethane layer was separated
3. 3
   ПромывкаThe dichloromethane layer was washed successively with 2 l each of water, twice with 2 l of 1 N hydrochloric acid
4. 4
   Концентрированиеtwice with 2 l each of a saturated aqueous sodium chloride solution, and then concentrated to dryness under reduced pressure

Методика

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.

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