tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate oxalate
[CAS# 1227382-01-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate
• Name: tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate oxalate
• Molecular Formula: C₁₂H₂₀N₂O₆
• Molecular Weight: 288.30
• CAS Registry Number: 1227382-01-5
• SMILES: CC(C)(C)OC(=O)N1CC2(C1)CNC2.C(=O)(C(=O)O)O

Safety Data

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

Discovory and Applicatios

Tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylic acid oxalate, commonly abbreviated as TBDSH-oxalate, is a compound that has attracted attention in medicinal chemistry and materials science. It has a spirocyclic framework that combines structural rigidity with versatility, making it a useful building block in various scientific fields.

The discovery of TBDSH-oxalate stems from the ongoing exploration of spirocyclic compounds. These molecules are known for their unique three-dimensional shapes and potential biological activities. Synthesized in the early 2000s, TBDSH-oxalate contains a spiro[3.3]heptane ring system linked to a tert-butyl ester and an oxalate counterion. This structure, characterized by its rigid, compact form and nitrogen-containing framework, has unique chemical properties that can be used in drug development and other applications.

TBDSH-oxalate is synthesized via multistep organic reactions, typically involving the formation of a spirocyclic core followed by tert-butyl esterification and formation of the oxalate salt. The oxalate moiety stabilizes the molecule, enhancing its solubility and making it easier to handle in various applications. The tert-butyl group protects the carboxylate functionality, allowing for selective reactions in other parts of the molecule.

TBDSH-oxalate is primarily used as an intermediate in drug synthesis. Its spirocyclic structure is central to creating complex drug molecules with enhanced stability and bioavailability. Researchers have exploited its unique shape and reactivity to design drugs that can effectively interact with biological targets, particularly in the development of antiviral and anticancer drugs.

In drug discovery, TBDSH-oxalate has been used to develop protease inhibitors. These inhibitors are essential for treating diseases where proteases play a role, such as HIV/AIDS and certain cancers. The spirocyclic structure of TBDSH-oxalate provides a rigid scaffold that can effectively mimic the transition state of protease substrates, resulting in potent inhibition.

The backbone of this compound is also used to design new antibacterial agents. The rigidity and functional diversity of the spirocyclic system allow for the creation of molecules that can interact with bacterial enzymes and disrupt their function, providing a potential solution to antibiotic resistance.

In materials science, TBDSH-oxalate is used to synthesize novel polymers. Its spirocyclic core imparts mechanical strength and thermal stability to the polymer chain, making it suitable for high-performance applications such as advanced coatings and composites.

The unique structure of TBDSH-oxalate can also be used in organocatalysis. As a catalyst, it can facilitate a variety of organic transformations, including asymmetric synthesis, and its rigid chiral structure helps achieve high selectivity and efficiency in chemical reactions.

The current study explored the potential of TBDSH-oxalate in creating new therapeutic agents and materials. Its structural versatility and reactivity offer opportunities for innovation in chemical synthesis and drug development. The researchers continue to study its properties and applications, aiming to expand its use in different scientific fields.