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Compound 2 was made as a potential anti-HIV agent, based on its structural similarity to other reported anti-HIV compounds (Synthesis 2014, 46, 879-886). One of the early steps in the synthesis involved the creation of an ether group (highlighted) in compound 1. Identify reagents that you could use to prepare compound 1 via a Williamson ether synthesis. NH₂ PMBO PMBO m Many steps HO HO 2

Compound 2 was made as a potential anti-HIV agent, based on its structural similarity to other reported anti-HIV compounds (Synthesis 2014, 46, 879-886). One of the early steps in the synthesis involved the creation of an ether group (highlighted) in compound 1. Identify reagents that you could use to prepare compound 1 via a Williamson ether synthesis. NH₂ PMBO PMBO m Many steps HO HO 2

Chemistry
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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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**Select reagents that can be used to make the ether group of compound 1:** - **NaOMe** ![First compound](PMBO) Structure: The compound has a hydroxyl group (OH) at the end of a carbon chain which includes an alkyne group (triple bond) and an epoxide with "PMBO" groups. - **NaH** ![Second compound](PMBO) Structure: The compound has a hydroxyl group (OH) at the end of a carbon chain which includes an alkyne group (triple bond) and an epoxide with "PMBO" groups. - **Br group** ![Third compound](Bromine derivative 1) Structure: The compound is an alkyl bromide, with bromine (Br) attached to the terminal carbon of an alkene group (double bond). ![Fourth compound](Bromine derivative 2) Structure: The compound is an alkyl bromide, with bromine (Br) attached to the terminal carbon of an alkene group (double bond). **Note:** The text can be represented in plain text format complemented with chemical structures for better understanding in a classroom or educational website setting. The depiction of molecular structures is crucial for explaining chemical reactions and understanding reagent interactions.
Transcribed Image Text:**Select reagents that can be used to make the ether group of compound 1:** - **NaOMe** ![First compound](PMBO) Structure: The compound has a hydroxyl group (OH) at the end of a carbon chain which includes an alkyne group (triple bond) and an epoxide with "PMBO" groups. - **NaH** ![Second compound](PMBO) Structure: The compound has a hydroxyl group (OH) at the end of a carbon chain which includes an alkyne group (triple bond) and an epoxide with "PMBO" groups. - **Br group** ![Third compound](Bromine derivative 1) Structure: The compound is an alkyl bromide, with bromine (Br) attached to the terminal carbon of an alkene group (double bond). ![Fourth compound](Bromine derivative 2) Structure: The compound is an alkyl bromide, with bromine (Br) attached to the terminal carbon of an alkene group (double bond). **Note:** The text can be represented in plain text format complemented with chemical structures for better understanding in a classroom or educational website setting. The depiction of molecular structures is crucial for explaining chemical reactions and understanding reagent interactions.
### Synthesis of Compound 2 as a Potential Anti-HIV Agent #### Overview Compound 2 was synthesized as a potential anti-HIV agent due to its structural similarity to previously reported anti-HIV compounds. The detailed study is referenced in *Synthesis (2014, 46, 879-886)*. #### Key Step: Creation of Ether Group One of the early steps in the synthesis of Compound 2 involved the formation of an ether group, which is highlighted in compound 1. This key step can be achieved through a Williamson ether synthesis. #### Task Identify the reagents required for the preparation of compound 1 via Williamson ether synthesis. #### Diagram Explanation The diagram outlines the following: 1. **Compound 1 Structure**: - This compound contains the PMBO group, which stands for p-Methoxybenzyl ether, a common protecting group in organic synthesis. - An O-ether group is highlighted in green in the structure, signifying its importance in the synthesis process. - The steps leading to compound 2 are collectively referred to as "Many steps." 2. **Conversion to Compound 2**: - Through various chemical reactions, compound 1 is converted into the final product, compound 2, which possesses potential anti-HIV activity. - The structure of compound 2 includes the preserved ether linkage and has an additional NH2 amino group and a bicyclic ring system. 3. **Protecting Group (PMB)**: - The PMB group is structurally represented, showing its composition involving an aromatic ring with a methoxy group (OCH3) attached. #### Reagent Identification For the preparation of compound 1 via the Williamson ether synthesis, the following reagents are typically required: 1. **Alcohol or Phenol Reactant**: - The starting material provides the hydroxyl group (-OH) which will be converted into the ether. 2. **Alkyl Halide or Sulfonate**: - This reactant contains the alkyl group (R) which will be attached to the oxygen atom (O) of the alcohol/phenol through a nucleophilic substitution reaction. These reagents and the conditions under which they react (e.g., base conditions) typically determine the efficiency and yield of the Williamson ether synthesis, leading to the desired protection and formation of compound 1. This step-by-step approach underscores the importance of ether formation in the broader context of
Transcribed Image Text:### Synthesis of Compound 2 as a Potential Anti-HIV Agent #### Overview Compound 2 was synthesized as a potential anti-HIV agent due to its structural similarity to previously reported anti-HIV compounds. The detailed study is referenced in *Synthesis (2014, 46, 879-886)*. #### Key Step: Creation of Ether Group One of the early steps in the synthesis of Compound 2 involved the formation of an ether group, which is highlighted in compound 1. This key step can be achieved through a Williamson ether synthesis. #### Task Identify the reagents required for the preparation of compound 1 via Williamson ether synthesis. #### Diagram Explanation The diagram outlines the following: 1. **Compound 1 Structure**: - This compound contains the PMBO group, which stands for p-Methoxybenzyl ether, a common protecting group in organic synthesis. - An O-ether group is highlighted in green in the structure, signifying its importance in the synthesis process. - The steps leading to compound 2 are collectively referred to as "Many steps." 2. **Conversion to Compound 2**: - Through various chemical reactions, compound 1 is converted into the final product, compound 2, which possesses potential anti-HIV activity. - The structure of compound 2 includes the preserved ether linkage and has an additional NH2 amino group and a bicyclic ring system. 3. **Protecting Group (PMB)**: - The PMB group is structurally represented, showing its composition involving an aromatic ring with a methoxy group (OCH3) attached. #### Reagent Identification For the preparation of compound 1 via the Williamson ether synthesis, the following reagents are typically required: 1. **Alcohol or Phenol Reactant**: - The starting material provides the hydroxyl group (-OH) which will be converted into the ether. 2. **Alkyl Halide or Sulfonate**: - This reactant contains the alkyl group (R) which will be attached to the oxygen atom (O) of the alcohol/phenol through a nucleophilic substitution reaction. These reagents and the conditions under which they react (e.g., base conditions) typically determine the efficiency and yield of the Williamson ether synthesis, leading to the desired protection and formation of compound 1. This step-by-step approach underscores the importance of ether formation in the broader context of
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