Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)?What are the important criteria of a good resolving reagent?In particular why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen NH3NH2(S,S) Salt- Insoluable in Aqueous SolutionForms PrecipitateCH3HORacemic-(+)-Ibuprofen(S)-(-)-methylbenzyl amineCH3NH3(R,S) Salt- Soluable in Aqueous Solution CH3CH3H2SO4NH3(S)-(+)-ibuprofen(not water soluable)(S,) SaltNH3HSO4ammonium salt(water soluable)Oll.

The separation of two enantiomers is called a resolution.

Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)? What are the important criteria of a good resolving reagent? In particular why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen

Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)? What are the important criteria of a good resolving reagent? In particular why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter18: Carboxylic Acids

Section: Chapter Questions

Problem 18.54P

See similar textbooks

Related questions

Q: Explain the role of trisodium citrate, Na3C6H5O7 as a component of the Benedict’s reagent for the…

A: A question based on redox reactions in qualitative analysis of organic sample, which is to be…

Q: Thalidomide is a chiral molecule and it was identified that the R-isomer produced the sedative…

A: Thalidomide is a chiral molecule and it was identified that the R-isomer produced the sedative…

Q: Explain Separation of an isomeric mixture?

A: Isomers: Isomers are compounds having same molecular formula but different structural and Optical…

Q: The separate enantiomers. of 2-hydroxyheptanoic acid were needed for determination of the absolute…

A: Given reagent is (R) or (S)-malic acid.

Q: Explain the process of Calculating Enantiomeric Excess ?

A: The absolute difference between the mole fraction of two enantiomers is termed as enantiomers.

Q: GLYCEROL CH03 LOD 50 D. 4000 3000 2000 1500 1000 500 HAVENUMBERI -

A: Glycerol is a compound with three alcohol groups. It can be basically called a triol

Q: The method of assay for sulfonamides is? Kjeldahl method Diazotization method Gravimetric…

A: The solution is given below -

Q: B When a chiral compound is dissolved in water the observed rotation is 8.4°. If the specific…

Q: In which period lactinides and actinides are placed?

A: Lanthanides and actinides are in periods 6 and 7, respectively

Q: The (R) enantiomer of a pure compound has optical rotation [a], 25 = 60.0⁰. If a sample is 66.6% R…

A: The R enantiomer of a pure compound has optical rotation of 60.0° . A sample is 66.6 % R and 33.3…

Q: SOLUBILITY TEST distilled water Litmus paper test OBSERVATIONS clear, colorless solution no change…

A: A question based on qualitative analysis, which is to be accomplished.

Q: ) Why would an unstabilized vlide tend to form more of the Z-stereoisomer?

Q: Search the standard of Bendroflumethiazide and its tablets USP. •What kind of method applied in the…

A: "Since there are multiple sub-parts in this question and it is not mentioned that which one has to…

Q: 12. Using a suitable example, explain (using structures) what is meant by a meso compound. Draw the…

Q: 7. Dihydrocarveol is another natural product found in spearmint oil, but in minor amounts.…

A: The given compound is dihydrocarveol. It is naturally found in caraway oil and mint oil. It is a…

Q: What is the coupling pattern for HA ? Singlet doublet of doublet dectet etc.

A: Splitting pattern of hydrogen in 1H-NMR follows the n+1 rule. Where, n= number of neighbouring…

Q: What strategy did McGregor & Hughes use to differentiate stereoisomers of nerolidol by GCXGC-MS?

A: When the molecules have the same bonding pattern of the groups besides having the same molecular…

Q: Draw a resonable structure for a complex between Fe3+ and nitrilotriacetic acid

A: Fe+3 contains 3d3 4s0 valency electronic configuration and it makes an octahedral geometry when it…

Q: Give the Summary of the Factors That Determine AmineBasicity ?

A: Amines are able to accept a hydrogen atom by donating a lone electron pair, making them a base in…

Q: Why is it necessary to resolve Chiral pharmaceuticals why can't we just use racemic versions in the…

A: The separation of the components of a racemic mixture is called chiral resolution. It is helpful for…

Q: ) Draw tge HY^3- species of EDTA to illustrate that it is a Zwitterion

A: As per the Bartley expert guidelines, I am allowed to answer FIRST one question at a time. Sorry,…

Q: Does the Enalapril molecule follow Lipinskis rules? why or why not? H

A: Lipinski's rules: It is the set of rules that have to be obeyed by the molecule in order to consider…

Q: Explain why fac' isomer shows onlv one methyl signal whereas 'mer' isomer shows three methyl signals…

A: Transition metal complexes or coordination metal complexes are formed by arrangement of groups of…

Q: create a separations flow chart for Sb3+, Fe3+, Zn2+, Al3+, Cd2+ without using sulfides or…

Q: (a) Put in order of increasing rate of substitution by NH; in the following complexes (a)…

A: In a substitution reaction, the rate of reaction depends upon the M-OH2 bond strength which directly…

Q: Cuen about radox Reaction Determine the inner Sphere pathway & for the roduction of azidopentaammine…

Q: What kind of differences are there in crystallizing in unit cell with 1. Chiral (enantiomerically…

A: A chiral compound is distinguished from its mirror images as these are non-superimposable. A chiral…

Q: While (S)-ibuprofen is the active ingredient, commercial ibuprofen is sold as a racemic drug because…

A: The research's lab product contains 94 % enantiomeric excess of the S product. Therefore, the…

Q: Draw a well labeled outline showing how the resolution of ibuprofen process worked and then fully…

A: The process by which enantiomers Of racemic Compound separated is called stereochemical Resolution.…

Q: Can you give an example of homotopic, heterotopic, enantiotopic, and diastereotopic for compounds?

A: Topicity is the stereochemical relationship between substituents and the structure to which they are…

Q: Expain by calculating formal chages why the following acd-base complexes have the charges indicated…

A: Formal charge is calculated as – F.C = number of valence electrons - number of non bonded electrons…

Q: Two enantiomers can be separated by the process of resolution. Describe How ?

A: Two enantiomers can be separated by the process of resolution has to be described below.

Q: A solution of a chiral compound was prepared by dissolving 15.67 g in 16.00 mL of solvent. The…

A: Given data: Observed rotation = 62.41° Path length = 1.00 dm Mass of compound = 15.67 g Volume of…

Q: What is the commercial use of ibuprofen? 2. What are the important criteria of a good resolving…

A: 1) Commercial use: It is used to relieve pain from various conditions like - headache,…

Q: Is it possible to resolve a racemic mixture of 1-phenylethylamine with (-)-malic acid?

A: Find answer next steps

Q: Mescaline (see structure X) is a naturally-occuring psychedelic compound isolated from the peyote…

A: In organic laboratories, acid-base extraction involves the extraction of an organic compound using…

Q: All heteroaroms (atoms that are not carbons or hydrogens) should he considered part of a pi system.…

A: Imidacloprid is a systemic insecticide which belong to a class of neonicotinoids. This is an insect…

Q: Describe what the purpose of making a "derivative" like a semicarbizides, phenyhydrazin or DNP…

A: The purpose of making derivative like DNP solid is for the fact that it is used to distinguish the…

Q: 5. Which of the following materials (B- E) could be used to carry out the optical resolution of…

A: Whenever a particular enantiomer is needed in pure form, an optically pure chiral molecule can be…

Q: What, if anything, would happen to the absorbance of a FeSCN2+ solution, if the FeSCN2+ solution was…

A: The Beer-Lambert law states, for a given material sample path length and concentration of the sample…

Q: Results and Discussion: Nitroprusside Reaction: Samples: cysteine, cystine, glycine Reagents:…

A: Interpretation: To write results and discussion for the Nitroprusside reaction

Q: What is the changes in TZDs (specifically pioglitazone) structure that has direct impact in clinical…

A: The thiazolidinediones are TZDs or glitazones belong to a class of antidiabetic drugs and improve…

Q: Provide an illustration of resolution of a racemate mixture using diasteromer formation.

A: We have to illustration of resolution of racemate mixture using diasteromer formation.

Q: B Tert-butyl chloride in AICI3 was added in each test tube containing compounds A, B, and C. Which…

A: Q-1 Tert-butyl chloride with AlCl3 is a type of friedel -crafts alkylation reaction. This reaction…

Q: Is it possible to prepare a 17% dye solution from a 4% stock dye solution? Explain your answer.

A: Given : Stock solution with concentration = 4 % (Assuming by mass) And concentration of solution to…

Q: Is it possible to prepare a 17% dye solution from a 4% dye solution? Explain.

A: If the solution is too weak in terms of concentration, we can evaporate some of the solvent to make…

Question

Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)?

What are the important criteria of a good resolving reagent?

In particular why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen

NH3
NH2
(S,S) Salt- Insoluable in Aqueous Solution
Forms Precipitate
CH3
HO
Racemic-(+)-Ibuprofen
(S)-(-)-methylbenzyl amine
CH3
NH3
(R,S) Salt- Soluable in Aqueous Solution

CH3
CH3
H2SO4
NH3
(S)-(+)-ibuprofen
(not water soluable)
(S,) Salt
NH3
HSO4
ammonium salt
(water soluable)
Oll.

Expert Solution

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!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Why is it necessary to resolve chiral pharmaceuticals (why cant we just use racemic versions)?

VIEW

What are the important criteria of a good resolving reagent?

VIEW

Why is (S)- methylbenzylamine a suitable resolving agent for ibuprofen

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 4 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

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.

Similar questions

Selective serotonin reuptake inhibitors (SSRIs) are commonly prescribed antidepressants. SSRIs block the reabsorption of the neurotransmitter serotonin in the brain. Changing the balance of serotonin helps brain cells send and receive chemical messages, which in turn boosts mood. Two SSRI medications are Faverin (fluvoxamine, C15H21F3N2O2 ) and Zoloft (sertraline, C17H17Cl2N ). Determine the molar masses of Faverin and Zoloft
Given the Ka values (in parentheses) for the following acids: HSO4– (Ka= 1.2 x 10–2); HNO2 (Ka= 4.0 x 10–4); HC2H3O2 (Ka= 1.8 x 10–5); Calculate Kc values for the following acid-base equilibria: (a) HSO4–(aq) + C2H3O2–(aq) ⇌ HC2H3O2(aq) + SO42–(aq) (b) HC2H3O2(aq) + NO2–(aq) ⇌ HNO2(aq)+ C2H3O2–(aq)
Draw the structures of the following derivatives :(i) Propanone oxime (ii) Semicarbazone of CH3CHO
On the following page are three compounds, 1, 2, and 3, that have been investigated as anti-malarial candidates. Compound 1 is the "parent" molecule, and 2 and 3 are derivatives. Shown next to each molecule is (i) the enthalpy change when it binds to its target, and (ii) the dissociation constant for the molecule/target complex. Consider the structures and answer the following: AH = - 1.2 kcal/mol; Kp = 16 nM OH 1 HO AH = - 6.0 kcal/mol; Kp = 76 nM OH AH = - 5.5 kcal/mol; Kp = 0.5 nM OH 3 (i) What is the difference among 1, 2, and 3?
5. Which of the following equations shows that isoquinoline, C9H;N, behaves as a Bronsted-Lowry base in water? a) CóH;N(aq) + H2O(1) = b) CH;N(aq) + H2O(1) c) C9H;N(aq) + OH¯(aq) = d) CoH;N(aq) + H;O*(aq) e) CoH;NH*(aq) + H2O(!) C9H;NH*(aq) + OH (aq) = C9H&N°(aq) + H;O*(aq) C9HN¯(aq) + H;O(!) = C9H;NH*(aq) + H2O(1) = C9H;N(aq) + H;O*(aq)
3. (a) The optical rotation [a]20 of aqueous samples of pure a-D-glucose and 1 pure ß-D-glucose were measured over time and a graph plotted (below). The optical rotation of both samples tends towards the same value, +52.7, as time proceeds. Explain, with the use of a diagram, why this trend is observed. +112 [a] +52.7 +19 Time
5. (Chapter 15 - Q41b) Propose a structure for the compound that fits the following description. C30H14 7.0 8, (4H, broad singlet) 2.85 (1H, septet J = 8 Hz) 1.20 5 (6H, doublet J=8 Hz) 2.28 6 (3H, singlet) IR: 825 cm 1 5(a) Degree of the unsaturation of this compound is= 5(b) Two peaks at 2.85 o and 1.20 õ indicate that the compound has. group = 4(c) A peak at 2.28 õ indicates that the compound has. group= 4(d) IR absorption indicates the compound is .-disubstituted = 4(e) The name of the compound is =
7.) Which of the following is the product of CH,CHO + [Ag(NH3)2J* + OH- – product + Ag + H,0 + NH3 (1) CH,COO- (2) CH,CH,O (3) CH,COOA9 (4) CH;O-
Draw structural formulas for the following compounds: (a) Tributylamine(b) N-methylanilinium chloride(c) ethylammonium chloride (d) 2-amino-1-pentanol(e) 3,3-dimethyl-N-phenyl-2-aminohexane (f) 1,2-ethanediamine
Draw the structure of the following three isomeric amides with chemical formula CGH|NO. Amide #1: N-ethylcyclopropanecarboxamide Amide #2: (Z)-3-hexenamide Amide #3: N-methylcyclobutanecarboxamide • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. P opy aste ChemDoodle®
Which of the follwoing compounds is responsible for the mass sepctrum and why? (a) octanol, CH3CH2CH2CH2CH2CH2CH2CH2OH (b) heptane, CH3CH2CH2CH2CH2CH2CH3 (c) acetic acid, CH3COOH
(b) (d) CH3 CH3CHCH₂CH₂CH₂Br SCH₂CH3 1. (NH₂)₂C=S 2. NaOH, H₂O H₂O2, H₂O, ? ?