Hydrochloric Acid → HCID 178448381, compound

HRID 2043796Notes

Reaction equation

HRID 2043796 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>[Pd].C(O)(C)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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178448377HCID 178448377, compound

Product 1

HCID 178448381HCID 178448381, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Hydrochloric acid (13 g) and 10% palladium on carbon (5.5 g) was added to a solution of mono-benzyloxycarbonyl-L-valine ganciclovir (50 g) in 23% aqueous iso-propanol (Iso-propanol:water::500 mL:150 mL). The reaction mixture was hydrogenated at about 25° C. to 40° C. under hydrogen pressure of 0.5-1 kg/cm2 for about 1 hour. After completion of the reaction, the reaction mass was filtered and washed with iso-propanol:water mixture (Iso-propanol:water::45 mL:5 mL). Iso-propanol (500 mL) was added over a period of about 1 hour. The reaction mass was cooled to 0° C., maintained at about 0° C. to about −5° C. for about 1 hour, filtered, washed with 10% aqueous iso-propanol solution (50 mL) followed by washing with iso-propanol (50 mL) and dried to obtain valganciclovir hydrochloride (31 g).

Workup

  1. customwas hydrogenated at about 25° C. to 40° C. under hydrogen
  2. customfor about 1 hour
  3. customAfter completion of the reaction
  4. filtrationthe reaction mass was filtered
  5. washwashed with iso-propanol
  6. additionIso-propanol (500 mL) was added over a period of about 1 hour
  7. temperaturemaintained at about 0° C. to about −5° C. for about 1 hour
  8. filtrationfiltered
  9. washwashed with 10% aqueous iso-propanol solution (50 mL)
  10. washby washing with iso-propanol (50 mL)
  11. customdried

Sources & evidence

ORD record
ord-239e2ae221014e43bee75825cd557a94
Source dataset
uspto-grants-2013_11
Patent number
US08586738B2

Reaction notes

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