반응 #65670

반응 방정식

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

용매

pyridine

반응 조건

후처리

1. 1
   기타Under a nitrogen atmosphere, in a round-bottom flask were placed
2. 2
   기타the 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
   여과The 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
   추출extracted with several portions of chloroform
9. 9
   건조The chloroform extracts were dried (Na2SO4)
10. 10
    농축concentrated with a rotary evaporator
11. 11
    세척the crude product was rinsed with ether
12. 12
    기타recrystallized from ethanol-water

실험 절차

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.

출처