Duloxetine or Cymbaltaandreg; (1) is a serotonin-norepinephrine reuptake inhibitor (SNRI) prescribed for major depressive disorder, generalized anxiety disorder, fibromyalgia and neuropathic pain. A racemic mixture of Duloxetine (2) is dissolved in a mixture of toluene and methanol to which solution is also added optically active mandelic acid (3). Sodium hydroxide is added to obtain the final product (5). Which of the following statements most accurately describes the role of the various compounds?a)Compound 4 is the (S,S) diastereomeric salt made from the ammonium and mandelate ion and separated by precipitation.b)Compound 4 is the protonated form of the alcohol group, protonated at the oxygen.c)Compound 5 is R-isomer of Duloxetine and precipitates upon deprotonation with sodium hydroxide.d)Compound 3 is (R)-mandelic acid and is considered a chiral resolving agent.Correct answer is option 'A'. Can you explain this answer?

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a)
Compound 4 is the (S,S) diastereomeric salt made from the ammonium and mandelate ion and separated by precipitation.
b)
Compound 4 is the protonated form of the alcohol group, protonated at the oxygen.
c)
Compound 5 is R-isomer of Duloxetine and precipitates upon deprotonation with sodium hydroxide.
d)
Compound 3 is (R)-mandelic acid and is considered a chiral resolving agent.

Correct answer is option 'A'. Can you explain this answer?

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Duloxetine or Cymbalta® (1) is a serotonin-norepinephrine reuptake...

Here we have a mechanism for chiral resolution for the drug Duloxetine. Generally, a racemic mixture is resolved into its enantiomer through a chiral resolving agent.

The chiral resolving agent here is mandelic acid without having assigned stereochemistry. The molecule that is shown is (S)-mandelic acid. It will protonate the amine group in the Duloxetine.

Upon protonation, the ammonium ion is formed, and mandelic acid becomes the mandalate ion. There are two diastereomeric salts formed, (R)-Duloxetine-(S)-mandalate and (S)-Duloxetine-(S)-mandalate.

Compound 5 needs to have the stereochemistry assigned, which is (S)-mandelic acid.

Compound 4 is the (S,S) diastereometric salt and can be separated by precipitation, leaving (R)-Duloxetine behind.

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Duloxetine or Cymbalta® (1) is a serotonin-norepinephrine reuptake inhibitor (SNRI) prescribed for major depressive disorder, generalized anxiety disorder, fibromyalgia and neuropathic pain. A racemic mixture of Duloxetine (2) is dissolved in a mixture of toluene and methanol to which solution is also added optically active mandelic acid (3). Sodium hydroxide is added to obtain the final product (5). Which of the following statements most accurately describes the role of the various compounds?a)Compound 4 is the (S,S) diastereomeric salt made from the ammonium and mandelate ion and separated by precipitation.b)Compound 4 is the protonated form of the alcohol group, protonated at the oxygen.c)Compound 5 is R-isomer of Duloxetine and precipitates upon deprotonation with sodium hydroxide.d)Compound 3 is (R)-mandelic acid and is considered a chiral resolving agent.Correct answer is option 'A'. Can you explain this answer?

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Duloxetine or Cymbalta® (1) is a serotonin-norepinephrine reuptake inhibitor (SNRI) prescribed for major depressive disorder, generalized anxiety disorder, fibromyalgia and neuropathic pain. A racemic mixture of Duloxetine (2) is dissolved in a mixture of toluene and methanol to which solution is also added optically active mandelic acid (3). Sodium hydroxide is added to obtain the final product (5). Which of the following statements most accurately describes the role of the various compounds?a)Compound 4 is the (S,S) diastereomeric salt made from the ammonium and mandelate ion and separated by precipitation.b)Compound 4 is the protonated form of the alcohol group, protonated at the oxygen.c)Compound 5 is R-isomer of Duloxetine and precipitates upon deprotonation with sodium hydroxide.d)Compound 3 is (R)-mandelic acid and is considered a chiral resolving agent.Correct answer is option 'A'. Can you explain this answer? for MCAT 2024 is part of MCAT preparation. The Question and answers have been prepared according to the MCAT exam syllabus. Information about Duloxetine or Cymbalta® (1) is a serotonin-norepinephrine reuptake inhibitor (SNRI) prescribed for major depressive disorder, generalized anxiety disorder, fibromyalgia and neuropathic pain. A racemic mixture of Duloxetine (2) is dissolved in a mixture of toluene and methanol to which solution is also added optically active mandelic acid (3). Sodium hydroxide is added to obtain the final product (5). Which of the following statements most accurately describes the role of the various compounds?a)Compound 4 is the (S,S) diastereomeric salt made from the ammonium and mandelate ion and separated by precipitation.b)Compound 4 is the protonated form of the alcohol group, protonated at the oxygen.c)Compound 5 is R-isomer of Duloxetine and precipitates upon deprotonation with sodium hydroxide.d)Compound 3 is (R)-mandelic acid and is considered a chiral resolving agent.Correct answer is option 'A'. Can you explain this answer? covers all topics & solutions for MCAT 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Duloxetine or Cymbalta® (1) is a serotonin-norepinephrine reuptake inhibitor (SNRI) prescribed for major depressive disorder, generalized anxiety disorder, fibromyalgia and neuropathic pain. A racemic mixture of Duloxetine (2) is dissolved in a mixture of toluene and methanol to which solution is also added optically active mandelic acid (3). Sodium hydroxide is added to obtain the final product (5). Which of the following statements most accurately describes the role of the various compounds?a)Compound 4 is the (S,S) diastereomeric salt made from the ammonium and mandelate ion and separated by precipitation.b)Compound 4 is the protonated form of the alcohol group, protonated at the oxygen.c)Compound 5 is R-isomer of Duloxetine and precipitates upon deprotonation with sodium hydroxide.d)Compound 3 is (R)-mandelic acid and is considered a chiral resolving agent.Correct answer is option 'A'. Can you explain this answer?.

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