6. The molecule below is (loosely) inspired by a recently disclosed Phase III clinical candidate drug used to treat refractory chronic cough. Propose three unique retrosynthetic disconnections on this molecule, clearly mark them, then show the intermediates and reagents (if appropriate) that would be used to synthesize the molecule in a forward direction. You can choose to disconnect the final product at three unique positions, or can further retrosynthetically disconnect intermediates from previous fragments. F
6. The molecule below is (loosely) inspired by a recently disclosed Phase III clinical candidate drug used to treat refractory chronic cough. Propose three unique retrosynthetic disconnections on this molecule, clearly mark them, then show the intermediates and reagents (if appropriate) that would be used to synthesize the molecule in a forward direction. You can choose to disconnect the final product at three unique positions, or can further retrosynthetically disconnect intermediates from previous fragments. F
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
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.42P
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Concept explainers
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
Question
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#### Explanation:
The provided diagram depicts a complex molecule with various functional groups which include a piperidine ring, a fluorobenzyl group, and an oxazolidinone group. The structure showcases potential points for retrosynthetic disconnections, characterized by breaking bonds to simplify the molecule into easily synthesizable fragments.
**Key Structural Features:**
1. Piperidine ring
2. Benzene ring with fluorine substituents
3. Multiple ester and amide linkages
**Steps and Considerations for Retrosynthetic Analysis:**
1. **Identify Functional Groups:** Identify all functional groups and significant segments of the molecule which can represent potential sites for disconnection.
2. **Possible Disconnection Sites:**
- Between the oxazolidinone and the benzene ring.
- Between the benzene ring and the fluorinated substituents.
- Within the ester linkages connecting the cyclic structures.
3. **Reassemble Synthesizable Units:** Consider how these simpler units could be reassembled using standard organic synthesis methods.
**Detailed Analysis:**
**Marked Disconnections:**
- Disconnection 1: Between the benzene ring and the piperidine ring.
- Disconnection 2: Between the fluorine-substituted benzene ring and the methoxy group.
- Disconnection 3: Within the ester linkage connecting the oxazolidinone.
---
*This problem involves applying principles of retrosynthetic analysis to break down a complex molecule into simpler precursor units for easier and efficient synthesis, critical in drug discovery and development.*](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Feb2e2013-15d0-4e81-b731-8816ed407a57%2F61338240-f958-4111-99dc-33b1236e3295%2F1oi37f_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Retrosynthetic Analysis in Drug Discovery
#### Problem Statement
The molecule below is (loosely) inspired by a recently disclosed Phase III clinical candidate drug used to treat refractory chronic cough.
**Task:** Propose three unique retrosynthetic disconnections on this molecule, clearly mark them, then show the intermediates and reagents (if appropriate) that would be used to synthesize the molecule in a forward direction. You can choose to disconnect the final product at three unique positions, or can further retrosynthetically disconnect intermediates from previous fragments.
---
---
#### Explanation:
The provided diagram depicts a complex molecule with various functional groups which include a piperidine ring, a fluorobenzyl group, and an oxazolidinone group. The structure showcases potential points for retrosynthetic disconnections, characterized by breaking bonds to simplify the molecule into easily synthesizable fragments.
**Key Structural Features:**
1. Piperidine ring
2. Benzene ring with fluorine substituents
3. Multiple ester and amide linkages
**Steps and Considerations for Retrosynthetic Analysis:**
1. **Identify Functional Groups:** Identify all functional groups and significant segments of the molecule which can represent potential sites for disconnection.
2. **Possible Disconnection Sites:**
- Between the oxazolidinone and the benzene ring.
- Between the benzene ring and the fluorinated substituents.
- Within the ester linkages connecting the cyclic structures.
3. **Reassemble Synthesizable Units:** Consider how these simpler units could be reassembled using standard organic synthesis methods.
**Detailed Analysis:**
**Marked Disconnections:**
- Disconnection 1: Between the benzene ring and the piperidine ring.
- Disconnection 2: Between the fluorine-substituted benzene ring and the methoxy group.
- Disconnection 3: Within the ester linkage connecting the oxazolidinone.
---
*This problem involves applying principles of retrosynthetic analysis to break down a complex molecule into simpler precursor units for easier and efficient synthesis, critical in drug discovery and development.*
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