Ganciclovir Mono-O-acetate Chemical Properties

Melting point:

194-197°C

Density 

1.66±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.32±0.20(Predicted)

color 

White

Ganciclovir Mono-O-acetate Usage And Synthesis

Chemical Properties

White Solid

Uses

Ganciclovir derivative.

Synthesis

The general procedure for the synthesis of 2-((2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy)-3-hydroxypropyl acetate from 1-acetylimidazole and 2-amino-9-(((1,3-dihydroxypropan-2- yl)oxy)methyl)-1H-purin-6(9H)-one is as follows: 500.0 g (1.96 mol, 1.0 equiv) of ganciclovir, 244.4 g (2.35 mol, 1.2 eq.) of trimethyl borate and 7.5 kg of toluene were added to the reaction vessel and heated to reflux for 5 hours. The progress of the reaction was monitored by TLC to confirm the complete reaction of the ingredients. The reaction mixture was cooled to room temperature and 396.7 g (3.93 mol, 2.0 eq.) of triethylamine was added, followed by 323.7 g (2.94 mol, 1.5 eq.) of 1-acetylimidazole, and stirred for 6 hours at room temperature. The ratio of monoacetyl ganciclovir to N,O-diacetyl ganciclovir was analyzed by HPLC to be 94:4. The reaction mixture was cooled to 0-10 °C and 2.0 kg of methanol was slowly added dropwise followed by stirring for 2 h at room temperature. The solvent was removed by concentration under reduced pressure, 3.0 kg of ethyl acetate was added, the organic layer was washed with 500 g of water and the aqueous layer was extracted with 500 g of ethyl acetate. The organic layers were combined, concentrated under reduced pressure and recrystallized by ethanol to give 440.9 g of colorless crystal product in 75.7% yield and 99.2% purity.

References

[1] Patent: CN108383840, 2018, A. Location in patent: Paragraph 0033; 0034; 0043; 0045; 0050
[2] Patent: CN108503642, 2018, A. Location in patent: Paragraph 0028-0034; 0039; 0040; 0042-0050; 0053; 0054
[3] Patent: CN108503641, 2018, A. Location in patent: Paragraph 0030; 0031; 0033; 0034; 0040-0051; 0054; 0055
[4] Patent: CN108409739, 2018, A. Location in patent: Paragraph 0033; 0034; 0043; 0045; 0050

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