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Related Concept Videos

Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.5K
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...
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Preparation of Amides01:29

Preparation of Amides

4.1K
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...
4.1K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.4K
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...
4.4K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.6K
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...
3.6K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.1K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.1K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.7K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
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An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

Qing-Lan Pei1, Guan-Da Che1, Ru-Yi Zhu2

  • 1Asymchem Life Science (Tianjin) Co., Ltd. , 71 Seventh Avenue, TEDA, Tianjin 300457, PR China.

Organic Letters
|October 18, 2017
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A new method efficiently removes acidic amide auxiliaries using an epoxide-enabled alcoholysis. This cost-effective technique advances the development of versatile directing groups for C-H activation.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Acidic amide auxiliaries are crucial in organic synthesis.
  • Efficient removal of these auxiliaries is essential for broader application.

Purpose of the Study:

  • To develop a practical and efficient method for removing versatile acidic amide auxiliaries.
  • To establish a protocol applicable to various amide substrates and C-H functionalization products.

Main Methods:

  • Developed an epoxide-enabled alcoholysis protocol for amide auxiliary removal.
  • Utilized potassium acetate (KOAc) as a catalyst.
  • The mechanism is analogous to the Myers' auxiliary removal.

Main Results:

  • Achieved facile alcoholysis of diverse amide substrates.
  • Demonstrated high efficiency in removing auxiliaries from C-H functionalization products.
  • The method is characterized by low cost and high practicality.

Conclusions:

  • The developed protocol offers a significant advancement in amide auxiliary removal.
  • This method facilitates the use of a versatile directing group for C-H activation strategies.
  • The approach is efficient, cost-effective, and broadly applicable.