반응 #76251

반응 방정식

34

1-(2, 3, 4-Tri-O-benzoyl-β-D-ribopyranosyl)-5-(2-phtalimidoethyl)uracil

NaOMe

water

→

35

수율 93.4%

5-(2-Phtalimidoethyl)-1-(β-D-ribopyranosyl)uracil

수율 93.4%

용매

MeOH

반응 조건

후처리

1. 1
   기타overnight
2. 2
   workup.ADDITIONAmberlite IR-120 was added to the resulting suspension until the pH was <7
3. 3
   workup.DISSOLUTIONThe solid was dissolved in the presence
4. 4
   온도of heat
5. 5
   여과filtered off hot from the ion exchanger
6. 6
   세척washed with MeOH
7. 7
   기타After removing the solvent
8. 8
   온도This yielded 9 g of crude product, which was heated
9. 9
   온도under reflux in 90 ml of MeOH for 10 min
10. 10
    온도After cooling to room temp.
11. 11
    workup.ADDITIONthe mixture was treated with 60 ml of Et2O
12. 12
    여과Filtration
13. 13
    세척washing with Et2O
14. 14
    기타drying in an oil pump vacuum

실험 절차

15 g (20 mmol) of 34 were dissolved in 500 ml of MeOH in a 1 l round-bottomed flask, treated with 324 mg (6 mmol) of NaOMe and stirred at room-temp. overnight with exclusion of water (TLC checking, AcOEt/n-heptane 1:1). Amberlite IR-120 was added to the resulting suspension until the pH was <7. The solid was dissolved in the presence of heat, filtered off hot from the ion exchanger and washed with MeOH. After removing the solvent, the residue was co-evaporated twice using 150 ml of water each time. This yielded 9 g of crude product, which was heated under reflux in 90 ml of MeOH for 10 min. After cooling to room temp., the mixture was treated with 60 ml of Et2O and stored overnight at 4° C. Filtration, washing with Et2O and drying in an oil pump vacuum yielded 7.8 g (93%) of 35.

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