Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-CoA reductase. In one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used. Draw the structure of synthetic intermediate A. ČI H3C- NaCN DMSO Но. Pyridine • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Should you want to restart the exercise, the drop-down menu labeled == starting points == can be used to redraw the starting molecule on the sketcher. opy aste H3C CH3 CHHS HO. Previous Next CH3

Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-CoA reductase. In one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used.

**Task:**
Draw the structure of synthetic intermediate A.

**Chemical Reaction:**
- A starting molecule with a hydroxyl group (OH), ester groups, and a pentyl side chain is given as the reactant.
- This reacts with a benzene ring having a sulfonyl chloride group in the presence of pyridine, resulting in intermediate A.
- Subsequent reaction with NaCN in DMSO leads to product B.

**Instructions:**
- Use the wedge/hash bond tools to indicate stereochemistry where it exists.
- If you wish to restart the exercise, the drop-down menu labeled "starting points" can be used to redraw the starting molecule on the sketcher.

**Sketcher Tools:**
- A toolbar is provided for drawing chemical structures, including tools for bonds, shapes, and stereochemistry.
- Options for copying, pasting, and rotating structures are also available.

This educational exercise involves understanding and applying concepts related to organic chemistry synthesis, stereochemistry, and mechanism drawing in a chemical sketching interface.
Transcribed Image Text:Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-CoA reductase. In one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used. **Task:** Draw the structure of synthetic intermediate A. **Chemical Reaction:** - A starting molecule with a hydroxyl group (OH), ester groups, and a pentyl side chain is given as the reactant. - This reacts with a benzene ring having a sulfonyl chloride group in the presence of pyridine, resulting in intermediate A. - Subsequent reaction with NaCN in DMSO leads to product B. **Instructions:** - Use the wedge/hash bond tools to indicate stereochemistry where it exists. - If you wish to restart the exercise, the drop-down menu labeled "starting points" can be used to redraw the starting molecule on the sketcher. **Sketcher Tools:** - A toolbar is provided for drawing chemical structures, including tools for bonds, shapes, and stereochemistry. - Options for copying, pasting, and rotating structures are also available. This educational exercise involves understanding and applying concepts related to organic chemistry synthesis, stereochemistry, and mechanism drawing in a chemical sketching interface.
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