Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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How do you deprotect the side-chain carboxyl under mild conditions without removing the BOC-protecting group at the same time?

The side-chain carboxyl groups of aspartic acid and glutamic acid are often protected as
benzyl esters.
Me,COČNHCHČOCH3
ВОС as amino-
protecting group
CH,
CH,
benzyl ester as carboxyl-
protecting group
C=0
ÓCH,Ph
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Transcribed Image Text:The side-chain carboxyl groups of aspartic acid and glutamic acid are often protected as benzyl esters. Me,COČNHCHČOCH3 ВОС as amino- protecting group CH, CH, benzyl ester as carboxyl- protecting group C=0 ÓCH,Ph
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The deprotection of the side chain carboxyl group (benzyl ester) can be done by the hydrogenolysis with H2 in presence of a metal catalyst palladium (pd) ) or platinum (pt) under mild conditions. 

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