HCID 178418361, compound → Didanosine

HRID 2354003Notes

Reaction equation

HRID 2354003 reaction equation
[Na].[C@@H:2]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([OH:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[CH:4]=[CH:3]1.[H][H]>[Ni].O>[CH:10]1[N:9]([C@@H:2]2[O:8][C@H:5]([CH2:6][OH:7])[CH2:4][CH2:3]2)[C:18]2[N:17]=[CH:16][NH:15][C:13](=[O:14])[C:12]=2[N:11]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178520965HCID 178520965, compound

Product 1

HCID 135398739DidanosineYield 66.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

2′,3′-Dideoxy-2′,3′-didehydroinosine sodium salt (50 gm) is added to water (180 ml) and stirred for 20 minutes at 25-35° C. Then the contents are hydrogenated under nitrogen atmosphere at 1.5-2.0 kg/cm2 hydrogen pressure at 15-20° C. using raney nickel catalyst for 7-8 hours. The reaction mass is filtered on a celite bed and washed with water (25 ml). To the filtrate activated carbon (2 gm) is added and stirred for 20 minutes. The mass is filtered on a celite bed and washed with water (25 ml). The filtrate is cooled to 5-15° C., the pH is adjusted to 7.0-8.0 with dilute hydrochloric acid (13 ml water+13 ml conc. HCl) at 5-15° C. and stirred for 2 hours 30 minutes. Filtered the mass, washed with water (40 ml). The resulting wet cake is added to water (120 ml), the temperature is raised to 65-75° C. and stirred for 20 minutes at the same temperature. The resulting solution is cooled to 25-35° C. and stirred for 1 hour 30 minutes. The reaction mass is then cooled to 10-15° C. and stirred for 1 hour 30 minutes. Filtered the solid, washed with the 40 ml of water and dried at 55-60° C. to give 30.5 gm of didanosine (HPLC Purity: 99.85%).

Workup

  1. customfor 7-8 hours
  2. filtrationThe reaction mass is filtered on a celite bed
  3. washwashed with water (25 ml)
  4. additionTo the filtrate activated carbon (2 gm) is added
  5. stirringstirred for 20 minutes
  6. filtrationThe mass is filtered on a celite bed
  7. washwashed with water (25 ml)
  8. temperatureThe filtrate is cooled to 5-15° C.
  9. customis adjusted to 7.0-8.0 with dilute hydrochloric acid (13 ml water+13 ml conc. HCl) at 5-15° C.
  10. stirringstirred for 2 hours 30 minutes
  11. filtrationFiltered the mass
  12. washwashed with water (40 ml)
  13. additionThe resulting wet cake is added to water (120 ml)
  14. temperaturethe temperature is raised to 65-75° C.
  15. stirringstirred for 20 minutes at the same temperature
  16. temperatureThe resulting solution is cooled to 25-35° C.
  17. stirringstirred for 1 hour 30 minutes
  18. temperatureThe reaction mass is then cooled to 10-15° C.
  19. stirringstirred for 1 hour 30 minutes
  20. filtrationFiltered the solid
  21. washwashed with the 40 ml of water
  22. customdried at 55-60° C.

Sources & evidence

ORD record
ord-111e3a9a02ab4ae09875794b32771fd6
Source dataset
uspto-grants-2010_07
Patent number
US07750153B2

Reaction notes

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