Production Method 1

7324-05-2

3082-75-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Ethanol ;  0 °C; overnight, 0 °C → reflux; reflux → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  15 min, 0 °C
1.3 Reagents: Nitric acid Solvents: Methanol ;  0 °C; 30 min, 0 °C

Reference

Amino acid-derived protic ionic liquids: physicochemical properties and behavior as amphiphile self-assembly media

Wang, Jiayi; et al, Australian Journal of Chemistry, 2011, 64(2), 180-189

Ethyl (2S)-2-Aminopropanoate Raw materials

• L-Alaninamide

Ethyl (2S)-2-Aminopropanoate Preparation Products

• Ethyl (2S)-2-Aminopropanoate (3082-75-5)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

Comprehensive Overview of Ethyl (2S)-2-Aminopropanoate (CAS No. 3082-75-5): Properties, Applications, and Industry Insights

Ethyl (2S)-2-Aminopropanoate, also known by its CAS number 3082-75-5, is a chiral ester derivative of alanine with significant relevance in pharmaceutical synthesis, flavor chemistry, and biochemical research. This optically active compound, characterized by its L-configuration at the alpha carbon, serves as a versatile building block in asymmetric synthesis and peptide modification. The growing demand for enantiomerically pure intermediates in drug development has positioned this compound as a critical tool for medicinal chemists exploring structure-activity relationships (SAR) and metabolic stability optimization.

Recent advancements in green chemistry methodologies have spotlighted Ethyl (2S)-2-Aminopropanoate as a model substrate for enzymatic esterification processes. Researchers are particularly interested in its role in biocatalytic transformations, where its high enantiomeric purity (>99% ee) enables precise control over stereochemical outcomes. The compound's balanced lipophilicity (logP ~0.5) and water solubility make it an ideal candidate for studying prodrug design strategies, a trending topic in pharmaceutical formulation circles addressing bioavailability challenges.

In flavor and fragrance applications, CAS 3082-75-5 contributes to the synthesis of fruit ester analogs, with emerging research exploring its potential in creating clean-label flavor enhancers. The food industry's shift toward natural-identical compounds has increased scrutiny on such chiral precursors. Analytical techniques like HPLC chiral separation and circular dichroism spectroscopy are routinely employed to verify the stereochemical integrity of this material, reflecting the compound's importance in quality control protocols.

The compound's crystalline form (typically appearing as white needles) exhibits remarkable stability under nitrogen atmosphere, making it suitable for long-term storage in research settings. Thermal analysis reveals a sharp melting point between 45-48°C, with decomposition occurring above 210°C. These physicochemical properties are frequently discussed in process chemistry forums, especially regarding scale-up challenges in multi-kilogram productions.

Patent literature analysis shows a steady increase in applications referencing Ethyl (2S)-2-Aminopropanoate, particularly in protease inhibitor development and neuromodulator synthesis. Its structural flexibility allows for diverse N-functionalization while preserving the stereocenter, a feature highly valued in structure-based drug design. Current Good Manufacturing Practice (cGMP) compliant routes to this compound are being optimized to meet the needs of clinical trial material production.

Environmental fate studies indicate that 3082-75-5 undergoes rapid biodegradation in aqueous systems, scoring favorably in green chemistry metrics assessments. This characteristic aligns with the pharmaceutical industry's growing emphasis on sustainable synthetic pathways. Regulatory databases classify the compound as non-hazardous under standard handling conditions, though proper laboratory hygiene practices are always recommended when working with amino acid derivatives.

Spectroscopic characterization of Ethyl (2S)-2-Aminopropanoate reveals distinctive features in both infrared spectroscopy (strong carbonyl stretch at 1740 cm?1) and proton NMR (triplet-quartet pattern characteristic of ethyl esters). These spectral signatures are frequently referenced in analytical method development for chiral purity assessment. The compound's specific rotation ([α]D2? ≈ +15° in ethanol) serves as a critical quality attribute in certificate of analysis documentation.

Emerging applications in peptide mimetics design have expanded the utility of this chiral synthon. Its ability to serve as a scaffold for constrained analogs makes it valuable in conformational restriction studies – a hot topic in GPCR-targeted drug discovery. The ethyl ester's protecting group strategy offers advantages in solid-phase peptide synthesis workflows, particularly when orthogonal deprotection is required.

Supply chain data indicates consistent global availability of CAS 3082-75-5, with manufacturers offering both research-grade and GMP-grade material. Pricing trends reflect the compound's position as a specialty chemical rather than a commodity item. Storage recommendations typically suggest 2-8°C under inert atmosphere for extended shelf life, though the material demonstrates good stability at room temperature for short-term use.

Academic interest in Ethyl (2S)-2-Aminopropanoate continues to grow, with recent publications exploring its use in dynamic kinetic resolutions and organocatalytic transformations. The compound's structural simplicity yet stereochemical complexity makes it an excellent model system for teaching asymmetric synthesis principles in graduate-level organic chemistry courses. Safety data sheets classify it as non-toxic at laboratory scales, though standard personal protective equipment should be employed as with all chemical handling.

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