2218437-05-7 | rac-(1r,3s)-3-({[(tert-butoxy)carbonyl]amino}methyl)-2,2-difluorocyclopropane-1-carboxylic acid

CAS:2218437-05-7 | rac-(1r,3s)-3-({[(tert-butoxy)carbonyl]amino}methyl)-2,2-difluorocyclopropane-1-carboxylic acid,Description

The compound contains a cyclopropane ring, which is a three-membered carbon ring. It also has a carboxylic acid group (-COOH), an amino group (-NH2), and a tert-butoxycarbonyl group (BOC group). The BOC group is commonly used in organic synthesis to protect amines.

Synthesis Analysis

The synthesis of similar compounds often involves the introduction of the tert-butoxycarbonyl (BOC) group into a variety of organic compounds using flow microreactor systems. This process is efficient, versatile, and sustainable compared to batch processes.

Chemical Reactions Analysis

The compound, due to the presence of the carboxylic acid and amino groups, can participate in a variety of chemical reactions. For example, the carboxylic acid group can undergo reactions such as esterification and amide formation. The amino group, especially when protected by the BOC group, can participate in reactions with carboxylic acids and other carbonyl-containing compounds.

Scientific Research Applications

Synthesis and Structural Analysis

• The compound has been a focal point in the diastereo- and enantioselective synthesis of 2-substituted 1-aminocyclopropane-1-carboxylic acids, serving as a precursor for protected 2,3-methano analogs of ornithine and glutamic acid. This synthesis facilitates access to multiple stereoisomers, underscoring its versatility in creating amino acid derivatives with potential biological activities (Frick, Klassen, & Rapoport, 2005).
• Researchers have employed the compound in the facile synthesis and highly efficient resolution of constrained cyclopropane analogs of phenylalanine. This process highlights its role in generating optically pure compounds on a multigram scale, showcasing its applicability in producing enantiomerically enriched amino acids (Jiménez, López, Oliveros, & Cativiela, 2001) .
• A study on its crystal and molecular structure provided insights into the conformational analysis of a derivative of 1-aminocyclopropanecarboxylic acid. The findings contribute to a deeper understanding of the stereochemistry and potential hydrogen bonding capabilities of such compounds, which are crucial for designing molecules with specific biological functions (Cetina, Hergold-Brundić, Raos, & Žuža-Mak, 2003).

Applications in Peptide Modification and Drug Discovery

• The compound's derivatives have been utilized in the deoxyfluorination of carboxylic acids to access acyl fluorides and amides, demonstrating its potential in modifying bioactive molecules to enhance their pharmacological properties (Wang, Wang, Huang, Ni, & Hu, 2021).
• It has also played a significant role in the stereospecific conversion of 1-aminocyclopropanecarboxylic Acid to ethylene by plant tissues, indicating its relevance in agricultural research and the study of plant growth regulators (Hoffman, Yang, Ichihara, & Sakamura, 1982).
• Furthermore, the compound has been instrumental in the C-alkylation of peptides containing aminomalonate and (amino)(cyano)acetate residues. This application highlights its utility in peptide chemistry for introducing side-chain modifications that can significantly alter peptide properties for therapeutic purposes (Matt & Seebach, 1998) .

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