Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)? What are the important criteria of a good resolving reagent? In particular why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)?

What are the important criteria of a good resolving reagent?

In particular why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen

NH3
NH2
(S,S) Salt- Insoluable in Aqueous Solution
Forms Precipitate
CH3
HO
Racemic-(+)-Ibuprofen
(S)-(-)-methylbenzyl amine
CH3
NH3
(R,S) Salt- Soluable in Aqueous Solution
Transcribed Image Text:NH3 NH2 (S,S) Salt- Insoluable in Aqueous Solution Forms Precipitate CH3 HO Racemic-(+)-Ibuprofen (S)-(-)-methylbenzyl amine CH3 NH3 (R,S) Salt- Soluable in Aqueous Solution
CH3
CH3
H2SO4
NH3
(S)-(+)-ibuprofen
(not water soluable)
(S,) Salt
NH3
HSO4
ammonium salt
(water soluable)
Oll.
Transcribed Image Text:CH3 CH3 H2SO4 NH3 (S)-(+)-ibuprofen (not water soluable) (S,) Salt NH3 HSO4 ammonium salt (water soluable) Oll.
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