Pivampicillin is a methylpivoxyl ester of ampicillin. It is prepared as a pro-drug to improve the lipophilic characteristics of the antibiotic and thus its bioavailability. In the body, the pivalic ester is hydrolyzed allowing the release of ampicillin. With this information: a) Draw the structure of ampicillin (the hydrolysis product of pivampicillin). b) Show the complete mechanism for the hydrolysis in acid medium of the ester (shown in red).

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter28: Biomolecules: Nucleic Acids
Section28.SE: Something Extra
Problem 38AP
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Pivampicillin is a methylpivoxyl ester of
ampicillin. It is prepared as a pro-drug to
improve the lipophilic characteristics of the
antibiotic and thus its bioavailability. In the
body, the pivalic ester is hydrolyzed allowing
the release of ampicillin. With this information:
a) Draw the structure of ampicillin (the
hydrolysis product of pivampicillin).
b) Show the complete mechanism for the
hydrolysis in acid medium of the ester (shown
in red).
NH2H
N
Pivampicillin
Transcribed Image Text:Pivampicillin is a methylpivoxyl ester of ampicillin. It is prepared as a pro-drug to improve the lipophilic characteristics of the antibiotic and thus its bioavailability. In the body, the pivalic ester is hydrolyzed allowing the release of ampicillin. With this information: a) Draw the structure of ampicillin (the hydrolysis product of pivampicillin). b) Show the complete mechanism for the hydrolysis in acid medium of the ester (shown in red). NH2H N Pivampicillin
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