Reacción #65670

Ecuación de reacción

9-((2R,3R,4S)-3,4-bis-hyroxymethyl-oxetan-2-yl)adenine

benzoyl chloride

→

6-benzamido-9-((2R,3R,4S) 3,4-bis(hydroxymethyl)-oxetan-2-yl)purine

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroUnder a nitrogen atmosphere, in a round-bottom flask were placed
2. 2
   Otrothe cold bath was removed
3. 3
   workup.ADDITIONThe reaction mixture was diluted with a small amount of acetone
4. 4
   workup.ADDITIONpoured into ice/water
5. 5
   FiltraciónThe resulting precipitate was collected by suction filtration
6. 6
   workup.ADDITIONtreated with 20 mL of 1M aqueous sodium hydroxide in 40 mL of DMF
7. 7
   workup.ADDITIONThe reaction mixture was diluted with saturated aqueous sodium bicarbonate
8. 8
   Extracciónextracted with several portions of chloroform
9. 9
   SecadoThe chloroform extracts were dried (Na2SO4)
10. 10
    Concentraciónconcentrated with a rotary evaporator
11. 11
    Lavadothe crude product was rinsed with ether
12. 12
    Otrorecrystallized from ethanol-water

Procedimiento

Under a nitrogen atmosphere, in a round-bottom flask were placed 2.5 g of 9-((2R,3R,4S)-3,4-bis-hyroxymethyl-oxetan-2-yl)adenine and 40 mL of pyridine. To the system, at 0° C., was added 4.6 g of benzoyl chloride, the cold bath was removed, and the reaction mixture was stirred at room temperature for 1 day. The reaction mixture was diluted with a small amount of acetone and poured into ice/water. The resulting precipitate was collected by suction filtration and treated with 20 mL of 1M aqueous sodium hydroxide in 40 mL of DMF. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted with several portions of chloroform. The chloroform extracts were dried (Na2SO4) and concentrated with a rotary evaporator, and the crude product was rinsed with ether and recrystallized from ethanol-water to obtain 6-benzamido-9-((2R,3R,4S) 3,4-bis(hydroxymethyl)-oxetan-2-yl)purine.

Fuente