Hydrochloric Acid → HCID 178448381, compound

HRID 2043797Notes

Reaction equation

HRID 2043797 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 77.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Hydrochloric acid (2.08 g) and 10% palladium on carbon (0.88 g, 50% wet) was added to a solution of mono-benzyloxycarbonyl-L-valine ganciclovir (8 g) in 30% aqueous iso-propanol (Iso-propanol:Water::64 mL:28 mL). The reaction mixture was flushed with nitrogen twice and hydrogenated at 35° 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 20% aqueous iso-propanol (Iso-propanol:Water::6.4 mL:1.6 mL). Iso-propanol (123.3 mL) was added at about 20° C. to 25° C. in about 1 hour. The reaction mass was cooled to about 10° C. to 15° C. and maintained for about 1 hour, filtered, washed with 10% aqueous iso-propanol solution (10 mL) followed by washing with iso-propanol (10 mL) and dried to obtain valganciclovir hydrochloride (4.8 g).

Workup

  1. customThe reaction mixture was flushed with nitrogen twice
  2. customhydrogenated at 35° C. to 40° C. under hydrogen
  3. customfor about 1 hour
  4. customAfter completion of the reaction
  5. filtrationthe reaction mass was filtered
  6. washwashed with 20% aqueous iso-propanol (Iso-propanol:Water::6.4 mL:1.6 mL)
  7. additionIso-propanol (123.3 mL) was added at about 20° C. to 25° C. in about 1 hour
  8. temperatureThe reaction mass was cooled to about 10° C. to 15° C.
  9. temperaturemaintained for about 1 hour
  10. filtrationfiltered
  11. washwashed with 10% aqueous iso-propanol solution (10 mL)
  12. washby washing with iso-propanol (10 mL)
  13. customdried

Sources & evidence

ORD record
ord-33ebd3de71414d6fb697e0e8b5afe500
Source dataset
uspto-grants-2013_11
Patent number
US08586738B2

Reaction notes

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