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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.1K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
3.1K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.8K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.8K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.5K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.5K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.7K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.7K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K

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Updated: Sep 13, 2025

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

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Base-promoted dynamic amide exchange: efficient access to isotopically enriched tertiary amides.

Quentin Lemesre1, Rémi Blieck1, Antoine Sallustrau1

  • 1Service de Chimie Bio-organique et Marquage, CEA, DMTS, Université Paris-Saclay Gif-sur-Yvette F-91191 France davide.audisio@cea.fr.

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This study introduces new, direct amide isotope labeling methods using transamidation and amide metathesis, improving efficiency for drug discovery and enabling waste recycling for sustainable chemistry.

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Spin Saturation Transfer Difference NMR SSTD NMR: A New Tool to Obtain Kinetic Parameters of Chemical Exchange Processes
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Area of Science:

  • Chemical synthesis
  • Isotope chemistry
  • Drug discovery

Background:

  • Amide isotope labeling is vital in pharmaceutical research and development.
  • Existing methods for labeling peptide bonds are often multi-step and inefficient.

Purpose of the Study:

  • To develop novel, direct strategies for amide isotope labeling.
  • To enhance the sustainability of isotope labeling techniques in chemistry.

Main Methods:

  • Investigated amide isotope exchange via transamidation and amide metathesis.
  • Optimized reaction conditions and explored substrate scope for direct labeling.
  • Demonstrated preliminary isotope-containing waste recycling.

Main Results:

  • Achieved direct labeling of both amine and carbonyl moieties within amide bonds.
  • Established optimized conditions for novel isotope exchange reactions.
  • Showcased the potential for recycling isotope-labeled chemical waste.

Conclusions:

  • The developed methods offer a more direct and efficient approach to amide isotope labeling.
  • These advancements contribute to more sustainable practices in isotope chemistry and drug development.
  • Waste recycling strategies highlight a path towards greener chemical processes.