Bis(L-Valine) Ester Ganciclovir TFA Salt synthesis

Yield:-

Reaction Conditions:

palladium in acetic acid;

Steps:

5.b (b)

(b) 2-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-1,3-propanediyl bis(L-valinate) A mixture of 0.722 g (1.0 mmol) of 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-1,3-propanediyl bis(N-((benzyloxy)carbonyl)-L-valinate) and 300 mg of 10% palladium on carbon in 10 mL of acetic acid was shaken in a Parr apparatus at ambient temperature at an initial pressure of 50 psi for 18 hours. The mixture was filtered through a pad of celite, washing the pad with acetic acid. The filtrate was evaporated at room temperature under pump vacuum giving a syrup (822 mg) which was dried at 100° C. with 1.0 mm pressure. The resulting glass turned to a solid on scraping with a spatula and was the desired 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-1,3-propanediyl bis(L-valinate). The compound gave satisfactory ¹ H NMR, ¹³ C, UV and Mass spectra.

References:

US5043339,1991,A