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Preparation of Amides

Preparation of Amides

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...

Preparation of Acid Anhydrides

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

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...

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

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Updated: Jun 12, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Cyclic peptide synthesis with thioacids.

Kaname Sasaki¹, David Crich

¹Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

Organic Letters

|June 24, 2010

Summary

This summary is machine-generated.

This study introduces a novel method for synthesizing cyclic peptides using C-terminal 9-fluorenylmethylthioesters in Boc chemistry. This approach enables efficient cyclization and demonstrates compatibility with various functional groups.

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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Published on: August 20, 2018

Area of Science:

Organic Chemistry
Peptide Chemistry
Synthetic Chemistry

Background:

Solution phase peptide synthesis is a cornerstone of medicinal chemistry.
Cyclic peptides offer unique structural and functional properties.
Developing efficient cyclization strategies remains an active research area.

Purpose of the Study:

To develop a novel method for synthesizing cyclic peptides.
To utilize C-terminal 9-fluorenylmethylthioesters in peptide synthesis.
To demonstrate the versatility and functional group compatibility of the method.

Main Methods:

Employing Boc chemistry for solution phase peptide synthesis.
Utilizing C-terminal 9-fluorenylmethylthioesters.
Deprotection with piperidine to yield a C-terminal thioacid.
Cyclization using Sanger's reagent.

Main Results:

Successful synthesis of cyclic penta- and hexapeptides.
Demonstrated synthesis of a cyclic glycopeptide.
Confirmed functional group compatibility with alcohols and carboxylic acids.

Conclusions:

C-terminal 9-fluorenylmethylthioesters are compatible with Boc chemistry.
The described method provides an efficient route to cyclic peptides.
This strategy is applicable to complex cyclic glycopeptides and diverse functional groups.