In certain clinical situations, there is need for an injectable B-blocker with a short biological half-life. The clue to development of such a drug was taken from the struc- ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of its amide) has no B-blocking activity. Substituting an ester for the amide group and lengthening the carbon side chain by one methylene group resulted in esmolol. Its ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under physiological conditions. This hydrolysis product has no B-blocking activity. OMe + CI HO NH2 4-Hydroxycinnamic acid Esmolol Isopropyl- amine Epichloro- hydrin
In certain clinical situations, there is need for an injectable B-blocker with a short biological half-life. The clue to development of such a drug was taken from the struc- ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of its amide) has no B-blocking activity. Substituting an ester for the amide group and lengthening the carbon side chain by one methylene group resulted in esmolol. Its ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under physiological conditions. This hydrolysis product has no B-blocking activity. OMe + CI HO NH2 4-Hydroxycinnamic acid Esmolol Isopropyl- amine Epichloro- hydrin
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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.60P
Related questions
Question
Propose a synthesis for esmolol from 4-hydroxycinnamic acid, epichlorohydrin, and isopropylamine
![In certain clinical situations, there is need for an injectable B-blocker with a short
biological half-life. The clue to development of such a drug was taken from the struc-
ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of
its amide) has no B-blocking activity. Substituting an ester for the amide group and
lengthening the carbon side chain by one methylene group resulted in esmolol. Its
ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under
physiological conditions. This hydrolysis product has no B-blocking activity.
OMe
+ CI
HO
NH2
4-Hydroxycinnamic
acid
Esmolol
Isopropyl-
amine
Epichloro-
hydrin](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa48247c0-5a67-476b-a8b5-1d89b626d917%2Fc6b658db-5238-45bd-81b6-5d7f3eb17565%2F423an2h.jpeg&w=3840&q=75)
Transcribed Image Text:In certain clinical situations, there is need for an injectable B-blocker with a short
biological half-life. The clue to development of such a drug was taken from the struc-
ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of
its amide) has no B-blocking activity. Substituting an ester for the amide group and
lengthening the carbon side chain by one methylene group resulted in esmolol. Its
ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under
physiological conditions. This hydrolysis product has no B-blocking activity.
OMe
+ CI
HO
NH2
4-Hydroxycinnamic
acid
Esmolol
Isopropyl-
amine
Epichloro-
hydrin
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Introduction to General, Organic and Biochemistry](https://www.bartleby.com/isbn_cover_images/9781285869759/9781285869759_smallCoverImage.gif)
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Introduction to General, Organic and Biochemistry](https://www.bartleby.com/isbn_cover_images/9781285869759/9781285869759_smallCoverImage.gif)
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning