The drug sildenafil, sold under the trade name Viagra, is a potent inhibitor of phos- phodiesterase V (PDE V), an enzyme found in high levels in the corpus cavernosum of the penis. Inhibitors of this enzyme enhance vascular smooth muscle relaxation and are used for treatment of male impotence. Following is an outline for a synthesis of sildenafil. H Me Me EtO N„H4 EtO (1) EtO НО (2) (3) (4) Pr Pr Pr Me Me Me Но H,N H,N (6) EtO (7) O,N H,N Pr Pr Pr Me Me Me H, Н. Н. EtO EtO EtO Pr Pr Pr 0=$=0 0=$=0 Sildenafil (Viagra) ČH3
The drug sildenafil, sold under the trade name Viagra, is a potent inhibitor of phos- phodiesterase V (PDE V), an enzyme found in high levels in the corpus cavernosum of the penis. Inhibitors of this enzyme enhance vascular smooth muscle relaxation and are used for treatment of male impotence. Following is an outline for a synthesis of sildenafil. H Me Me EtO N„H4 EtO (1) EtO НО (2) (3) (4) Pr Pr Pr Me Me Me Но H,N H,N (6) EtO (7) O,N H,N Pr Pr Pr Me Me Me H, Н. Н. EtO EtO EtO Pr Pr Pr 0=$=0 0=$=0 Sildenafil (Viagra) ČH3
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.63P
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Question
Show how the reagent for Step 6 can be prepared from salicylic acid
(2-hydroxybenzoic acid). Salicylic acid, the starting material for the synthesis of aspirin and a number of other pharmaceuticals, is readily available by the Kolbe carboxylation of phenol
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