Réaction #65670

Équation de réaction

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

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   AutreUnder a nitrogen atmosphere, in a round-bottom flask were placed
2. 2
   Autrethe 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
   FiltrationThe 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
   Extractionextracted with several portions of chloroform
9. 9
   SéchageThe chloroform extracts were dried (Na2SO4)
10. 10
    Concentrationconcentrated with a rotary evaporator
11. 11
    Lavagethe crude product was rinsed with ether
12. 12
    Autrerecrystallized from ethanol-water

Mode opératoire

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.

Source