Tenofovir Disoproxil Fumarate → Tenofovir Disoproxil

HRID 554465Notes

Reaction equation

HRID 554465 reaction equation
[CH3:1][C@@H:2]([O:14][CH2:15][P:16]([O:27][CH2:28][O:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])([O:18][CH2:19][O:20][C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[O:17])[CH2:3][N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH2:13])[C:7]=2[N:6]=[CH:5]1.C(/C(O)=O)=C\C(O)=O>C(O)(C)C>[CH3:1][C@@H:2]([O:14][CH2:15][P:16]([O:18][CH2:19][O:20][C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])([O:27][CH2:28][O:29][C:30]([O:32][CH:33]([CH3:34])[CH3:35])=[O:31])=[O:17])[CH2:3][N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH2:13])[C:7]=2[N:6]=[CH:5]1

Participants

3

Reactant 1

HCID 6398764Tenofovir Disoproxil Fumarate

Product 1

HCID 5481350Tenofovir Disoproxil

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

Tenofovir disoproxil fumarate (100 gms, 0.1574 moles) is suspended in Isopropyl alcohol (1100 ml) at 25-35° C. The suspension is heated to about 60° C. for clear solution. The obtained clear solution is maintained for 1 hr at 60-65° C. Slowly cooled the mass to 30° C. in 1 hr and again cooled to 8° C. and maintained for ½ hr at 8-10° C. The precipitated product is filtered and washed with chilled Isopropanol. The wet material is dried at 50-55° C. under vacuum to give Tenofovir disoproxil hemifumarate.

Workup

  1. temperatureThe obtained clear solution is maintained for 1 hr at 60-65° C
  2. temperatureSlowly cooled the mass to 30° C. in 1 hr
  3. temperatureagain cooled to 8° C.
  4. temperaturemaintained for ½ hr at 8-10° C
  5. filtrationThe precipitated product is filtered
  6. washwashed with chilled Isopropanol
  7. customThe wet material is dried at 50-55° C. under vacuum

Sources & evidence

ORD record
ord-b6d7f16544ed48a58a8e8dc979f03da4
Source dataset
uspto-grants-2011_11
Patent number
US08049009B2

Reaction notes

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