Boc-(R)-3-Amino-4-(2,4-dichlorophenyl)butyric acid (CAS: 269396-53-4) is a molecule of significant interest in organic chemistry, primarily due to its utility as a precisely engineered building block. Understanding its chemical structure and the methods employed for its synthesis is crucial for chemists who plan to buy and utilize it in their research and development projects.

Deconstructing the Chemical Structure

The name itself reveals key structural features:

  • Boc: This signifies the presence of the tert-butoxycarbonyl (Boc) protecting group on the amino moiety. The Boc group is widely used in peptide synthesis and organic chemistry to temporarily mask the reactivity of an amine, preventing unwanted side reactions during subsequent synthetic steps. It is easily removed under mild acidic conditions.
  • (R)-: This designation denotes the stereochemistry at the chiral center, specifically the (R)-configuration at the carbon atom bearing the amino group. This chirality is often essential for the biological activity of derived compounds, particularly in pharmaceuticals.
  • 3-Amino-4-(2,4-dichlorophenyl)butyric acid: This is the core amino acid structure. It’s a derivative of butyric acid with an amino group at the third carbon and a 2,4-dichlorophenyl group attached to the fourth carbon. The presence of two chlorine atoms on the phenyl ring influences the electronic and steric properties of the molecule.

The molecular formula is C15H19Cl2NO4, and its molecular weight is approximately 348.22 g/mol. The compound typically presents as a white to off-white solid or powder, with a purity often specified as greater than 97%.

Synthetic Approaches for Manufacturers

The synthesis of Boc-(R)-3-Amino-4-(2,4-dichlorophenyl)butyric acid requires careful control over stereochemistry. Manufacturers often employ asymmetric synthesis techniques. Common strategies may involve:

  • Chiral Pool Synthesis: Utilizing naturally occurring chiral starting materials and transforming them through a series of reactions.
  • Asymmetric Catalysis: Employing chiral catalysts to induce stereoselectivity during key bond-forming steps, such as hydrogenation or amination.
  • Resolution of Racemates: Synthesizing a racemic mixture and then separating the desired enantiomer using chiral chromatography or diastereomeric salt formation.

The Boc protection step is typically performed using di-tert-butyl dicarbonate (Boc anhydride) under basic conditions. Subsequent purification steps, such as recrystallization or chromatography, are crucial to achieve the high purity required by end-users who wish to buy this intermediate for demanding applications.

Importance for Buyers

For researchers and procurement managers looking to buy Boc-(R)-3-Amino-4-(2,4-dichlorophenyl)butyric acid, understanding its structure and synthesis helps in evaluating supplier quality. A reputable manufacturer will not only provide detailed specifications but also evidence of robust synthetic methods that ensure the compound's integrity and stereochemical purity. This knowledge empowers informed purchasing decisions, ensuring the success of downstream synthetic processes.