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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
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Research Update on Ethyl (1R,2S)-2-(boc-amino)cyclopentanecarboxylate (CAS: 1140972-29-7)

Ethyl (1R,2S)-2-(boc-amino)cyclopentanecarboxylate (CAS: 1140972-29-7) is a key intermediate in the synthesis of chiral compounds, particularly in the pharmaceutical industry. Recent studies have highlighted its importance in the development of novel therapeutic agents, including protease inhibitors and antiviral drugs. This research briefing provides an overview of the latest advancements related to this compound, focusing on its synthetic applications, biological relevance, and emerging trends in its utilization.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of Ethyl (1R,2S)-2-(boc-amino)cyclopentanecarboxylate as a precursor in the synthesis of potent hepatitis C virus (HCV) NS3/4A protease inhibitors. The research team optimized the stereoselective synthesis of this intermediate, achieving a high yield (85%) and enantiomeric excess (>99%). The study emphasized the compound's role in enhancing the pharmacokinetic properties of the final drug candidates, particularly in improving oral bioavailability.

In the field of oncology, a recent patent application (WO2023051234) disclosed the use of 1140972-29-7 in the development of small-molecule inhibitors targeting protein-protein interactions in cancer signaling pathways. The patent highlights the compound's versatility as a chiral building block for constructing constrained peptidomimetics, which show promise in disrupting oncogenic protein complexes. The structural rigidity imparted by the cyclopentane ring was found to be critical for maintaining target binding affinity while reducing metabolic instability.

Advances in continuous flow chemistry have also impacted the production of Ethyl (1R,2S)-2-(boc-amino)cyclopentanecarboxylate. A 2024 publication in Organic Process Research & Development described a scalable continuous manufacturing process that reduces reaction times from 24 hours to under 2 hours while maintaining excellent stereocontrol. This technological improvement addresses previous challenges in large-scale production, making the compound more accessible for drug discovery programs.

Analytical characterization of 1140972-29-7 has seen significant progress with the application of advanced techniques. Recent work employing cryo-electron microscopy and solid-state NMR has provided unprecedented insights into the molecular packing and polymorphic behavior of this compound. These findings are particularly relevant for formulation scientists working to optimize the physical properties of drug substances derived from this intermediate.

Looking forward, the pharmaceutical industry is increasingly exploring the use of Ethyl (1R,2S)-2-(boc-amino)cyclopentanecarboxylate in mRNA-based therapeutics. Preliminary studies suggest its potential as a modified nucleoside precursor for stabilizing therapeutic oligonucleotides. While this application is still in early stages, it represents an exciting new direction for this versatile chiral building block.

In conclusion, recent research continues to expand the applications of 1140972-29-7 in drug discovery and development. Its role as a key chiral intermediate remains firmly established, with new synthetic methodologies and emerging therapeutic applications ensuring its ongoing relevance in medicinal chemistry. Researchers working with this compound should pay particular attention to the latest developments in continuous manufacturing and analytical characterization techniques to maximize its potential in their work.

• 245115-20-2((1R,2R)-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate)
• 143617-95-2(Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate)
• 474759-26-7(Methyl (1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate)
• 247159-48-4(1,3-Cyclopentanedicarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(hydroxymethyl)-, dimethyl ester, (1R,3S,4S,5S)-rel- (9CI))
• 1402568-08-4(cis-Ethyl 2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylate)
• 1140972-31-1(Ethyl (1S,2R)-2-(boc-amino)cyclopentanecarboxylate)
• 267230-27-3(Trans-cyclohexanecarboxylic Acid, 2-(1,1-dimethylethoxy)carbonylamino-, methyl ester)
• 192385-82-3(methyl (1S,2S)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylate)
• 192385-81-2(trans-(1R,2R)-2-tert-butoxycarbonylaminocyclopentanecarboxylic acid ethyl ester)
• 267230-26-2(Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-,methyl ester, (1S,2R)-)