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Organic letters

Cyclopropanecarboxylic acid esters as potential prodrugs with enhanced hydrolytic stability.


PMID 18181639

Abstract

Esters of cyclopropanecarboxylic acid demonstrate a substantial increase in stability under both acid- and base-catalyzed hydrolytic conditions. Comparison of the stability of valacyclovir 13 with the cyclopropane analogue 14 shows that at 40 degrees C and pH 6 the half-life of 14 is >300 h while the value for 13 is 69.7 h. CBS-QB3 calculations on isodesmic reactions for transfer of groups from an alkane to an ester show that a cyclopropyl group provides hyperconjugative stabilization.

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C116602
Cyclopropanecarboxylic acid, 95%
C4H6O2