The foundation of scientific advancement, particularly in chemistry and pharmaceuticals, lies in the availability of precisely synthesized chemical intermediates. N-Boc-D-proline, identified by CAS number 37784-17-1, is one such indispensable compound. As a derivative of the amino acid D-proline, it features the tert-butoxycarbonyl (Boc) protecting group, making it highly valuable for controlled chemical reactions and the synthesis of complex organic molecules. This article explores its chemical properties, synthesis, and its critical role in various industries.

Chemical Profile and Synthesis of N-Boc-D-Proline

N-Boc-D-proline is characterized by its molecular formula C10H17NO4 and a molecular weight of approximately 215.25 g/mol. It typically presents as a white crystalline powder with a melting point in the range of 134-137 °C. The chemical name, N-(tert-Butoxycarbonyl)-D-proline, clearly describes its structure: a D-proline molecule with a Boc group attached to the nitrogen atom of the pyrrolidine ring. Its optical activity, [α]22/D +60° (c = 2, acetic acid), further confirms its specific stereochemistry.

The synthesis of N-Boc-D-proline is a well-established process, often involving the reaction of D-proline with di-tert-butyl dicarbonate (Boc2O) in the presence of a base, such as sodium bicarbonate, in a suitable solvent system like dioxane and water. The reaction conditions are carefully controlled to ensure high yield and purity of the protected product. Post-reaction work-up typically includes acidification, extraction into an organic solvent (like ethyl acetate), washing, drying, and concentration to yield the final white solid. This synthetic route ensures the production of a high-quality intermediate essential for downstream applications.

Industrial Applications and Sourcing

The primary utility of N-Boc-D-proline lies in its role as a versatile intermediate:

  • Pharmaceutical Synthesis: It is widely used in the preparation of various drug candidates, including those targeting enzymes like histone deacetylases (HDACs) and caspases. Its incorporation can impart specific pharmacological properties and is crucial for chiral drug development.
  • Peptide Chemistry: As a protected amino acid, it is fundamental in solid-phase peptide synthesis, enabling the precise assembly of peptide chains with desired D-proline sequences.
  • Fine Chemicals: Beyond pharmaceuticals, it serves as a valuable building block in the broader field of fine chemical manufacturing and custom synthesis projects.

For businesses seeking to purchase N-Boc-D-proline, identifying reliable manufacturers and suppliers is key. Companies often look for specifications such as u226598% purity and proper CAS number verification (37784-17-1). Many chemical manufacturers in China offer this product with high quality and competitive pricing, often providing detailed Certificates of Analysis (CoA) to confirm purity and batch consistency. Bulk quantities are available for industrial production, while smaller amounts cater to research needs.

In summary, N-Boc-D-proline is a crucial chemical intermediate whose reliable synthesis and availability support innovation across the pharmaceutical and chemical industries. Its precise chemical structure and versatile application make it a sought-after compound for advanced research and manufacturing.