6-(tert-Butyloxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane
[CAS# 869494-16-6]

Identification

• Classification: API >> Antineoplastic agents
• Name: 6-(tert-Butyloxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane
• Synonyms: 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 198.26
• CAS Registry Number: 869494-16-6
• EC Number: 860-303-6
• SMILES: CC(C)(C)OC(=O)N1C2CC1CNC2

Properties

• Density: 1.104
• Boiling point: 276 °C
• Flash point: 121 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H228-H302-H312-H315-H319-H332-H335
• Safety Statements: P210-P240-P241-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable solids	Flam. Sol.	2	H228
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

6-(tert-Butyloxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane, commonly known as Boc-protected piperazine, was discovered in the mid-20th century as part of research into novel protecting groups for amino compounds. Chemists aimed to develop stable and selective protecting groups to shield specific functional groups during chemical transformations, particularly in peptide synthesis. Through systematic synthesis and screening, Boc-protected piperazine was identified as a suitable protecting group for the amino moiety in organic synthesis. Its discovery revolutionized peptide chemistry, enabling the efficient synthesis of complex peptides and proteins with precise control over amino acid sequences.

Boc-protected piperazine is widely used in peptide synthesis as a protecting group for the amino group (-NH2) of amino acids. By selectively masking the amino group with the Boc (tert-butyloxycarbonyl) group, unwanted side reactions can be prevented during peptide chain elongation, allowing for the synthesis of peptides with high purity and yield. Boc-protected piperazine is utilized in solid-phase peptide synthesis strategies, where peptides are synthesized on a solid support resin. The Boc group facilitates the stepwise assembly of peptides on the resin, enabling the rapid and efficient synthesis of peptide libraries and bioactive peptides for research and drug discovery.

Boc-protected piperazine plays a crucial role in the synthesis of peptide-based therapeutics and pharmaceutical intermediates. Peptide drugs, such as hormone analogs, enzyme inhibitors, and receptor agonists/antagonists, are synthesized using Boc chemistry, offering targeted and potent treatments for various diseases and disorders. Boc-protected piperazine is employed in protein engineering and bioconjugation techniques to modify and functionalize proteins with specific chemical groups or ligands. Site-specific incorporation of Boc-protected amino acids enables the introduction of desired functionalities into proteins, enhancing their stability, solubility, and bioactivity.

Boc-protected piperazine is used in protein labeling strategies to attach fluorophores, affinity tags, or reactive groups to specific amino acid residues in proteins. Site-specific labeling facilitates the visualization, purification, and manipulation of proteins in biochemical and cellular studies, elucidating their structure-function relationships and biological roles. Boc-protected piperazine derivatives are employed in chemical proteomics approaches to profile protein-ligand interactions and identify drug targets in complex biological systems. By conjugating small molecule probes to proteins via Boc chemistry, researchers can interrogate protein function and discover novel therapeutic agents.

References

2020. Selpercatinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-19-0140