N6-Cbz-L-lysine is an important amino acid derivative, and the detailed introduction is as follows:
Basic Information
Chemical formula: C₁₄H₂₀N₂O₄
CAS No.: 1155-64-2
Molecular weight: 280.32
Chemical name: 2-amino-6-(benzyloxycarbonylamino)hexanoic acid
Appearance: White to off-white solid powder
Physicochemical Properties
Solubility: Poorly soluble in ether solvents (can be precipitated using ether solvents); soluble in acidic and alkaline solutions, as well as organic solvents like ethanol.
Melting point: 250–260°C
Density: 1.206 g/cm³
Boiling point: 499.6°C (at 760 mmHg)
Flash point: 255.9°C
Synthesis Methods
The conventional synthesis starts from lysine and the acyl chloride of another fragment, forming the target product through an amide reaction between the amino group and acyl chloride. This process requires an external base (e.g., sodium hydroxide) as a acid-binding agent and careful control of the reactant ratio to selectively obtain the product from the terminal amino group reacting with acyl chloride, while preventing the amino group at the 2-position from participating in the reaction.
Applications
As a chiral organic synthesis intermediate, it is mainly used in the synthesis of chiral drug molecules and bioactive molecules. Its carboxyl group can undergo esterification in the presence of amino groups. Under acidic conditions, the benzyl-protected ester group can be easily removed to release the free carboxyl group. Additionally, the amino group can be converted into an azide group, introducing key fragments of the molecule into chiral drug molecules and bioactive molecules through click reactions.
Environmental Impact and Stability
As an organic amine, it poses significant hazards to water environments. Available data show that this compound has stable chemical properties, is not prone to deterioration, and avoids contact with oxidants. It does not decompose under normal conditions and does not undergo dangerous reactions.
