Hydrochloric Acid → HCID 178448381, compound

HRID 2043795Notes

Reaction equation

HRID 2043795 reaction equation
[ClH:1].C(OC([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])=O)C1C=CC=CC=1.[CH:20]1[N:24]([CH2:25][O:26][CH:27]([CH2:30]O)[CH2:28][OH:29])[C:23]2[N:32]=[C:33]([NH2:37])[N:34]=[C:35]([OH:36])[C:22]=2[N:21]=1.C(O)(C)C>[Pd].C(O)C>[CH3:16][CH:14]([C@H:13]([NH2:12])[C:17]([O:19][CH2:30][CH:27]([O:26][CH2:25][N:24]1[C:23]2[NH:32][C:33]([NH2:37])=[N:34][C:35](=[O:36])[C:22]=2[N:21]=[CH:20]1)[CH2:28][OH:29])=[O:18])[CH3:15].[ClH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178448377HCID 178448377, compound

Product 1

HCID 178448381HCID 178448381, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrochloric acid (2.6 g) and 10% palladium on carbon (1.1 g, 50% wet) were added to a solution of mono-benzyloxycarbonyl-L-valine ganciclovir (10 g) in aqueous ethanol (Ethanol:Water::96 mL:26 mL) at ambient temperature. The reaction mass was flushed with nitrogen twice and hydrogenated at about 35° C. to 40° C. under a hydrogen pressure of about 0.5-1 kg/cm2 for about 1 hour. The reaction mass was filtered and washed with 10% aqueous ethanol (10 mL). Ethanol was distilled out completely under reduced pressure at about 30° C. to 35° C. The residue was dissolved in water (6.25 mL) and stirred to obtain clear solution. Iso-propanol (56 mL) was added slowly over a period of about 1 hour. The reaction mass was cooled to about 10° C. to 15° C., maintained for about 1 hour, filtered, washed with 10% aqueous iso-propanol (10 mL) followed by washing with iso-propanol (10 mL) and dried to obtain valganciclovir hydrochloride (5.8 g).

Workup

  1. customThe reaction mass was flushed with nitrogen twice
  2. customhydrogenated at about 35° C. to 40° C. under a hydrogen
  3. customfor about 1 hour
  4. filtrationThe reaction mass was filtered
  5. washwashed with 10% aqueous ethanol (10 mL)
  6. distillationEthanol was distilled out completely under reduced pressure at about 30° C. to 35° C
  7. dissolutionThe residue was dissolved in water (6.25 mL)
  8. customto obtain clear solution
  9. temperatureThe reaction mass was cooled to about 10° C. to 15° C.
  10. temperaturemaintained for about 1 hour
  11. filtrationfiltered
  12. washwashed with 10% aqueous iso-propanol (10 mL)
  13. washby washing with iso-propanol (10 mL)
  14. customdried

Sources & evidence

ORD record
ord-385f282aa47b4233a2cd7707af5b608b
Source dataset
uspto-grants-2013_11
Patent number
US08586738B2

Reaction notes

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