In the intricate world of pharmaceutical synthesis, specific chemical intermediates serve as foundational building blocks, enabling the creation of complex and life-saving drugs. (S)-(+)-2-Chlorophenylglycine methyl ester tartrate stands out as one such compound, renowned for its pivotal role, especially in the production of clopidogrel, a blockbuster antiplatelet agent. Understanding its properties and applications is key for R&D scientists and formulation chemists.

Chemical Identity and Significance

(S)-(+)-2-Chlorophenylglycine methyl ester tartrate, identified by CAS number 141109-15-1, is a chiral compound that features a methyl ester of (S)-2-chlorophenylglycine paired with L-(+)-tartaric acid. This specific diastereomeric salt form is critical. The tartrate counterion helps to stabilize the chiral center, preventing racemization during storage and handling, which is a common challenge with enantiomerically pure compounds. The compound typically presents as a white to off-white crystalline solid, with a defined melting point and specific optical rotation, both essential parameters for confirming its enantiomeric purity and quality.

Advanced Synthesis Strategies

The production of enantiomerically pure intermediates has evolved significantly. While classical resolution methods using diastereomeric crystallization have been employed, they often suffer from low theoretical yields and high solvent consumption. More advanced techniques, such as attrition-enhanced deracemization, have revolutionized the synthesis. This method leverages mechanical grinding in a saturated solution, coupled with base-catalyzed racemization, to achieve near-quantitative yields and exceptionally high enantiomeric excess (>99.9% ee). These modern approaches are vital for manufacturers aiming to produce high-quality intermediates efficiently and sustainably.

Application in Clopidogrel Synthesis

The primary industrial application of (S)-(+)-2-Chlorophenylglycine methyl ester tartrate is its use as a stereochemical linchpin in the synthesis of clopidogrel. The (S)-configured alpha-carbon of the intermediate undergoes stereospecific transformations in subsequent reaction steps to form the final active pharmaceutical ingredient (API). This requires exceptional enantiomeric purity, typically above 99.5% ee, to ensure the desired pharmacological activity and avoid potential adverse effects from inactive or harmful enantiomers. The tartrate salt’s crystallinity aids in purification processes, allowing manufacturers to meet stringent regulatory standards.

Sourcing and Future Prospects

For pharmaceutical companies and contract manufacturers, securing a reliable supply of this critical intermediate is essential. When looking to buy, it’s important to partner with manufacturers who specialize in chiral chemistry and can demonstrate consistent quality and production capacity. Whether you are a research scientist exploring new drug candidates or a production manager scaling up manufacturing, understanding the specifications and sourcing strategies for compounds like (S)-(+)-2-Chlorophenylglycine methyl ester tartrate is key to success. If you are looking to purchase this intermediate, contacting reputable suppliers directly for a quote is the best approach to ensure you receive a high-quality product at a competitive price.