Hydrochloric Acid → HCID 178448381, compound

HRID 2043794Notes

Reaction equation

HRID 2043794 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].CO>[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 77.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

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 methanol (Methanol:Water::50 mL:8 mL) at ambient temperature. The reaction mass was flushed with nitrogen twice and hydrogenated at about 35° C. to 40° C. at hydrogen pressure of about 0.5-1 kg/cm2 for about 1 hour. The reaction mass was filtered and washed with methanol (10 mL). Methanol was distilled out completely under reduced pressure at about 30° C. to 35° C. The residue was dissolved in water (8 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 0 to 5° 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 (6 g).

Workup

  1. customThe reaction mass was flushed with nitrogen twice
  2. filtrationThe reaction mass was filtered
  3. washwashed with methanol (10 mL)
  4. distillationMethanol was distilled out completely under reduced pressure at about 30° C. to 35° C
  5. dissolutionThe residue was dissolved in water (8 mL)
  6. customto obtain clear solution
  7. temperaturemaintained for about 1 hour
  8. filtrationfiltered
  9. washwashed with 10% aqueous iso-propanol (10 mL)
  10. washby washing with iso-propanol (10 mL)
  11. customdried

Sources & evidence

ORD record
ord-1eefb4687ab5491a8d9734ca54f6c955
Source dataset
uspto-grants-2013_11
Patent number
US08586738B2

Reaction notes

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