Me Me Me Cl CI CI (A) (B) Diazepam Cl- Me CI 4-Chloro-N-methylaniline Benzoyl chloride

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.40P
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Diazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed,
diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the 2° amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous NaOH followed by careful acidification with HCl.

Q. Is diazepam chiral? If so, how many of the possible stereoisomers are formed in this synthesis?

Me
Me
Me
Cl
CI
CI
(A)
(B)
Diazepam
Cl-
Me
CI
4-Chloro-N-methylaniline
Benzoyl chloride
Transcribed Image Text:Me Me Me Cl CI CI (A) (B) Diazepam Cl- Me CI 4-Chloro-N-methylaniline Benzoyl chloride
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