Exploring solid-phase approaches for the preparation of new beta-lactams from amino acids
Related Experiment Video
Updated: Aug 29, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
Guillermo Gerona-Navarro1, Miriam Royo, Ma Teresa García-López
1Instituto de Química Médica (CSIC), Madrid, Spain.
Abstract:
Two solid-phase approaches, involving the base-assisted intramolecular alkylation of N-chloroacetyl-Phe derivatives anchored to appropriate solid supports, were investigated for the preparation of novel beta-lactams. When a BAL-type strategy was used, the resin-bound azetidinones were easily formed, as established by MAS-NMR, but final compounds could not be removed from the resin, unless a suitable two linkers system was used. In the second approach, in which the Phe residue is anchored to a Wang-type resin through the carboxylate group, the corresponding 1,4,4-trisubstituted 2-azetidinone was obtained in moderate to good yield and high purity.
More Related Videos
06:19An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
Published on: November 22, 2024
12:02An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
Published on: November 2, 2016
Related Concept Videos
Production of Antibiotics
Production of Pharmaceuticals
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Peptidoglycan Synthesis
Preparation of Amides
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 Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...