What Is N-[(S)-Ethoxycarbonyl-1-Butyl]-(S)-Alanine?

N-[(S)-Ethoxycarbonyl-1-Butyl]-(S)-Alanine is a chiral, N-alkylated amino acid derivative bearing two stereocenters, both in the (S) absolute configuration. Its structure combines an (S)-alanine backbone with an (S)-configured 1-butyl group that carries an ethoxycarbonyl (ethyl ester) substituent on the nitrogen atom.

This compound is best known in medicinal chemistry as a pivotal intermediate in the synthesis of Enalapril, a widely prescribed angiotensin-converting enzyme (ACE) inhibitor used in the management of hypertension and heart failure. The precise (S,S) stereochemistry is essential for the pharmacological activity of the final drug substance, making enantiomeric purity a critical quality attribute.

In the research setting, it also serves as a versatile chiral building block for the construction of peptidomimetics and other bioactive molecules that require a constrained, N-substituted amino acid motif.

Physicochemical Properties and Handling

N-[(S)-Ethoxycarbonyl-1-Butyl]-(S)-Alanine contains both a free carboxylic acid and an ethyl ester functional group, making it amphoteric and sensitive to both acidic and basic hydrolysis conditions. Researchers should avoid prolonged exposure to strongly acidic or strongly basic aqueous media to prevent racemization at the stereocenters or ester saponification.

The compound is typically handled as a solid or viscous oil depending on the lot. It is generally soluble in polar organic solvents such as methanol, ethanol, dimethyl sulfoxide (DMSO), and dimethylformamide (DMF), and shows limited solubility in non-polar solvents. Aqueous solubility is pH-dependent.

Standard laboratory precautions apply: wear appropriate personal protective equipment (PPE) including gloves, lab coat, and eye protection. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Avoid inhalation of dusts or aerosols.

Storage Conditions and Stability

To maintain chemical integrity and stereochemical purity, N-[(S)-Ethoxycarbonyl-1-Butyl]-(S)-Alanine should be stored in a tightly sealed container away from moisture, heat, and light. Refrigerated storage (2–8 °C) or freezer storage (−20 °C) is generally recommended for long-term preservation, depending on lot-specific guidance provided on the Certificate of Analysis (CoA).

Repeated freeze-thaw cycles should be minimized. If the compound has been dissolved in solvent, aliquoting into single-use portions before freezing is advised to preserve both chemical and stereochemical stability. Desiccant storage is recommended where the compound is hygroscopic.

Always refer to the CoA and SDS accompanying your specific lot for authoritative storage and shelf-life information, as these may vary between batches.

Applications in Research and Drug Synthesis

Pharmaceutical intermediate: The most prominent application of N-[(S)-Ethoxycarbonyl-1-Butyl]-(S)-Alanine is as a chiral dipeptide-like intermediate in the multi-step synthesis of Enalapril maleate and related ACE inhibitors. The correct (S,S) configuration is mandatory for optimal binding to the ACE active site.

Chiral building block: Medicinal chemists use this compound as a scaffold to introduce constrained N-alkylated amino acid residues into peptide-based drug candidates or peptidomimetics, enabling structure-activity relationship (SAR) studies.

Asymmetric synthesis research: The compound can serve as a reference substrate for evaluating new asymmetric N-alkylation or reductive amination methodologies, given that its stereocenters are well-characterized.

Analytical standard: Due to its defined stereochemistry, it may be employed as a reference standard in chiral HPLC method development for related pharmaceutical compounds.

Ordering, Specifications, and Quality Assurance

N-[(S)-Ethoxycarbonyl-1-Butyl]-(S)-Alanine is available from Aladdin Scientific under SKU N195204. Researchers should request the Certificate of Analysis (CoA) at the time of ordering to confirm lot-specific purity, stereochemical identity (optical rotation), and any analytical data such as HPLC purity, NMR characterization, and mass spectrometric confirmation.

For procurement teams, bulk quantities and custom pack sizes may be available upon request. Contact Aladdin Scientific's technical sales team for pricing, lead times, and volume discount information. All products are subject to Aladdin Scientific's standard terms and conditions regarding returns, refunds, and shipment.

If you have questions about regulatory documentation (e.g., REACH, RoHS compliance, or export requirements), please contact customer service directly. Material specifications are subject to change; always verify against the current CoA for your specific lot.