tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylate hemioxalate
[CAS# 1041026-71-4]

Identification

• Name: tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylate hemioxalate
• Synonyms: 2,6-Diazaspiro[3.3]heptane-2-carboxylic acid 1,1-dimethylethyl ester ethanedioate
• Molecular Formula: 2(C₁₀H₁₈N₂O₂).C₂H₂O₄
• Molecular Weight: 486.56
• CAS Registry Number: 1041026-71-4
• SMILES: CC(C)(C)OC(=O)N1CC2(C1)CNC2.CC(C)(C)OC(=O)N1CC2(C1)CNC2.C(=O)(C(=O)O)O

Properties

• Melting point: 206-209 °C^*

^* Burkhard, Johannes

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H315-H319-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate is a complex organic compound that has attracted attention for its role in medicinal chemistry and drug development. The compound has a spirocyclic structure and is a white to off-white crystalline powder that is soluble in organic solvents such as methanol, ethanol, and dichloromethane. The spirocyclic structure confers it with unique three-dimensional stability, enhancing its interaction with biological targets. It features a bicyclic system in which the nitrogen-containing ring is fused to the tert-butyl ester group.

The discovery of tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate is attributed to the efforts made in the late 20th and early 21st centuries to design novel spirocyclic skeletons for drugs. These compounds were designed to improve drug properties such as metabolic stability and receptor specificity. The study of spirocyclic compounds, including this derivative, is driven by the need for new chemical entities in drug discovery, especially for challenging therapeutic targets.

tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate is used as a core backbone in drug discovery, particularly in the design of enzyme inhibitors and receptor modulators. The spirocyclic framework of tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid enhances the binding affinity and selectivity of the compound for its biological target. It is used in medicinal chemistry to generate novel compounds with improved pharmacokinetic and pharmacodynamic properties. The incorporation of spirocyclic motifs often results in improved metabolic stability and increased oral bioavailability, which is of great value in the development of oral drugs.

tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate serves as an intermediate in the synthesis of complex molecules. Its structural rigidity and functional groups make it an excellent building block for the construction of a variety of chemical entities in synthetic organic chemistry. tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate serves as a template for reactions that require a rigid framework to maintain a specific spatial orientation of the functional groups. This is important in the stereoselective synthesis of molecules because the three-dimensional structure can be precisely controlled.

tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate is used as a biochemical probe to study enzyme function and protein-ligand interactions. These probes help elucidate the mechanisms of biological processes and the mode of action of potential drugs. It facilitates SAR studies by providing a stable core around which modifications can be made to study the relationship between chemical structure and biological activity.

tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate is incorporated into the design of advanced polymers. The rigidity and well-defined geometry of the spirocyclic core facilitates the development of polymers with unique physical and chemical properties, such as improved mechanical strength and thermal stability.

tert-Butyl 2,6-diazaspiro[3,3]heptane-2-carboxylic acid hemioxalate is a component of the prodrug strategy, acting as a carrier for active pharmaceutical ingredients (APIs). This approach can enhance the solubility, stability, and targeted delivery of drugs, thereby improving their therapeutic efficacy.

References

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