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Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation.

Tanya Román1,2,3,4, Gerardo Acosta3,4, Beatriz G de la Torre5

  • 1Núcleo Biotecnología Curauma, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, Chile.

Methods and Protocols
|September 22, 2023
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Summary

This study optimizes 2-chlorotrityl chloride (2-CTC) resin activation for solid-phase peptide synthesis (SPPS). The new method uses less thionyl chloride (SOCl2), reduces activation time, and allows resin reuse, improving yields for peptide synthesis.

Keywords:
2-CTC resin activation2-CTC resin reutilizationresin loadingsolid-phase peptide synthesis

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Materials Science

Background:

  • 2-chlorotrityl chloride (2-CTC) resin is crucial for solid-phase peptide synthesis (SPPS) of acid-terminated peptides.
  • This resin is sensitive to moisture, causing decreased loading and synthetic yields.
  • Standard activation with thionyl chloride (SOCl2) can be harsh and time-consuming.

Purpose of the Study:

  • To optimize the activation protocol for 2-CTC resin.
  • To minimize thionyl chloride (SOCl2) usage and activation time.
  • To assess the feasibility of reusing activated 2-CTC resin.

Main Methods:

  • Developed an optimized resin activation procedure using reduced amounts of thionyl chloride (SOCl2) in anhydrous dichloromethane (DCM).
  • Investigated varying concentrations of SOCl2 (2% and 25%) to achieve different activation degrees.
  • Evaluated the performance of reused 2-CTC resin following the optimized activation protocol.

Main Results:

  • Achieved significant resin activation with reduced SOCl2 and shorter reaction times (5 min).
  • Demonstrated successful reuse of 2-CTC resin with comparable synthetic yields to initial use.
  • Controlled activation levels: 2% SOCl2 yielded up to 44% activation (suitable for longer peptides), while 25% SOCl2 yielded up to 80% activation.

Conclusions:

  • The optimized protocol enhances 2-CTC resin activation efficiency and stability for SPPS.
  • Reduced reagent use and shorter activation times contribute to a more sustainable and cost-effective peptide synthesis process.
  • The ability to reuse the resin offers significant advantages for laboratory applications and scale-up.