Hydrochloric Acid → 6-Deoxypenciclovir

関与物質

反応条件

反応手順

24.21 g (0.1 mole) of 2-amino-9-(2-bromoethyl)purine was completely dissolved in 120 ml of dimethylsulfoxide, to which 48.05 g (0.3 mole) of diethylmalonate and 41.46 g (03 mole) of potassium carbonate were then added. The mixture was stirred at a temperature of 40-50° C. for 4 hours. After completion of the reaction, the reaction product was cooled to room temperature, to which 300 ml of water was then added. The solution was then extracted three times with 400 ml portions of dichloromethane. The organic layer was collected, and dried with anhydrous magnesium sulfate, followed by filtration and washing. The filtrate was concentrated under reduced pressure. The remaining concentrate was added to 300 ml of t-butanol and then warmed to 60° C., followed by the addition of 21.06 g (0.61 mole) of sodium borohydride. To the resulting mixture, 30 ml of methanol was added slowly, followed by stirring for five hours. After completion of the reaction, the reaction product was cooled to room temperature, neutralized with diluted hydrochloric acid, and then concentrated. The remaining concentrate was added to 100 ml of methanol and then stirred for two hours at room temperature, followed by filtration. The filtrate was concentrated under reduced pressure and crystallized from butanol, thereby giving 13.05 g (55% yield) of light yellow-colored 2-amino-9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purine.

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