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ChemicalBook CAS DataBase List Ganciclovir Mono-O-acetate
88110-89-8

Ganciclovir Mono-O-acetate synthesis

7synthesis methods
-

Yield: 75.2%

Reaction Conditions:

Stage #1:ganciclovir with triethyl borate in 2-methyltetrahydrofuran for 3 h;Reflux;Large scale;
Stage #2:vinyl acetate with triethylamine at 20; for 6 h;Large scale;
Stage #3: in ethanol at 0 - 20; for 3 h;Large scale;Reagent/catalyst;Solvent;

Steps:

3
500.0 g (1.96 mol, 1.0 eq) of ganciclovir, 314.7 g (2.15 mol, 1.1 eq) of triethyl borate,5.0 kg of 2-methyltetrahydrofuran was added to the reaction vessel, and heated to reflux for 3 hours.The TLC controlled raw material reacted completely to room temperature.595.0 g (5.88 mol, 3.0 eq) of triethylamine was added, and then 421.8 g (4.9 mol, 2.5 eq) of vinyl acetate was added, and the mixture was stirred at room temperature for 6 hours.The ratio of monoacetyl ganciclovirand N,O-diacetyl ganciclovir in the HPLC was 93/5, and the temperature was lowered by 0-10 °C.2.0 kg of ethanol was added dropwise, and the mixture was stirred at room temperature for 3 hours, and the solvent was concentrated under reduced pressure.It was washed once with 500 g of water, and the layers were separated.The ethanol was recrystallized to obtain 438.0 g of colorless crystals, the yield was 75.2%, and the purity was 99.1%.

References:

Anhui Haikang Pharmaceutical Co., Ltd.;Zhang Xiaoshun CN108383840, 2018, A Location in patent:Paragraph 0029; 0035; 0036; 0038; 0052

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