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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azetidines Azetidinecarboxylic acids or derivatives Azetidinecarboxylic acids

Recent Advances in the Application of tert-Butyl 3-aminoazetidine-1-carboxylate hydrochloride (CAS: 1210273-37-2) in Chemical Biology and Pharmaceutical Research

The compound tert-Butyl 3-aminoazetidine-1-carboxylate hydrochloride (CAS: 1210273-37-2) has recently garnered significant attention in chemical biology and pharmaceutical research due to its versatile applications as a key intermediate in drug discovery. This heterocyclic azetidine derivative serves as a crucial building block for the synthesis of various bioactive molecules, particularly in the development of kinase inhibitors and GPCR-targeted therapeutics. Recent studies highlight its role in facilitating the introduction of the azetidine moiety, a privileged scaffold known to enhance metabolic stability and improve pharmacokinetic properties of lead compounds.

Emerging literature from 2023-2024 demonstrates novel synthetic methodologies employing this compound. A study published in Journal of Medicinal Chemistry (2023) detailed its use in a microwave-assisted amide coupling reaction to generate potent PI3Kδ inhibitors with improved selectivity profiles. The hydrochloride salt form (1210273-37-2) was particularly noted for its enhanced solubility in polar aprotic solvents compared to the free base, enabling more efficient reactions at millimolar concentrations. Researchers at several pharmaceutical companies have incorporated this building block into their fragment-based drug discovery platforms, citing its optimal balance between ring strain and conformational flexibility.

Structural biology insights have revealed that derivatives synthesized from 1210273-37-2 exhibit unique binding modes with protein targets. Cryo-EM studies of a KRASG12C inhibitor containing this azetidine core demonstrated unexpected water-mediated hydrogen bonding networks that contributed to sub-nanomolar affinity. The tert-butoxycarbonyl (Boc) protecting group in particular allows for selective deprotection under mild acidic conditions, enabling sequential functionalization strategies that are becoming increasingly important in PROTAC and molecular glue development.

Recent ADMET studies of compounds derived from this intermediate show promising results. A 2024 ACS Pharmacology & Translational Science publication reported that azetidine-containing analogs displayed 3-5 fold improvements in metabolic stability in human liver microsomes compared to their pyrrolidine counterparts, with no significant CYP450 inhibition up to 10 μM concentrations. These findings validate the growing pharmaceutical interest in this chemotype for CNS-penetrant compounds, where the azetidine's reduced basicity (pKa ~7.2) may offer advantages over more traditional saturated nitrogen heterocycles.

Industrial applications of 1210273-37-2 have expanded significantly, with current Good Manufacturing Practice (cGMP) kilogram-scale production now established at multiple CDMOs. Process chemistry innovations have reduced the synthetic steps from commercially available starting materials from 7 to 4 steps, with overall yields improving from 32% to 68% through optimized Boc protection and hydrochloride salt formation conditions. These advances have made this building block more accessible for large-scale drug development programs, particularly in oncology and immunology pipelines.

Looking forward, researchers are exploring the potential of 1210273-37-2 in emerging therapeutic modalities. Preliminary data suggests its utility in covalent inhibitor design through incorporation of electrophilic warheads at the 3-position, while maintaining favorable physicochemical properties. Additionally, its application in peptide mimetics and macrocyclic compounds is being actively investigated, with several candidates currently in preclinical development stages. The unique spatial orientation of substituents enabled by the azetidine scaffold continues to provide novel opportunities in addressing challenging drug targets.

• 792970-55-9(1-(TERT-BUTOXYCARBONYL)-3-(DIMETHYLAMINO)AZETIDINE)
• 454703-23-2(tert-Butyl 3-(ethylamino)azetidine-1-carboxylate)
• 193269-78-2(tert-butyl 3-aminoazetidine-1-carboxylate)
• 454703-20-9(tert-Butyl 3-(methylamino)azetidine-1-carboxylate)
• 1158758-77-0(Tert-butyl 3-amino-3-methylazetidine-1-carboxylate)
• 313657-42-0(4-N-BOC-2-methylpiperazine Hydrochloride)
• 1000853-53-1((R)-1-N-Boc-2-methyl Piperazine Hydrochloride)
• 887581-43-3(tert-butyl 3-{[2-(dimethylamino)ethyl]amino}azetidine-1-carboxylate)
• 577777-20-9(tert-butyl N-(azetidin-3-yl)-N-methylcarbamate)
• 943060-59-1(tert-butyl N-(azetidin-3-yl)-N-methylcarbamate hydrochloride)