Chemical Identity and Structure

Benzyl (S)-(2-oxoazepan-3-yl)carbamate consists of a seven-membered lactam ring (azepan-2-one, also known as a caprolactam skeleton) bearing a pendant amine at the 3-position in the S absolute configuration. The amine is protected as a benzyloxycarbonyl (Cbz) carbamate, one of the most widely used and easily removable amine protecting groups in organic synthesis.

The compound combines two important functional handles: (1) the lactam carbonyl, which can participate in ring-opening or further elaboration reactions, and (2) the Cbz-protected amine, which is orthogonally deprotectable by catalytic hydrogenolysis under mild conditions. This dual functionality makes the molecule a versatile chiral synthon.

Applications in Synthesis

This compound serves primarily as a chiral building block in the construction of complex nitrogen-containing molecules. Key application areas include:

• Peptidomimetics: The azepanone scaffold mimics a dipeptide turn structure and is incorporated into peptidomimetic backbones to modulate protease resistance and conformational rigidity.
• Macrocyclic Drug Candidates: Seven-membered lactams are recurring motifs in macrocyclic protease inhibitors and other biologically active macrocycles; this building block provides an enantiopure entry point.
• Heterocyclic Synthesis: The lactam nitrogen and carbonyl can be functionalized to access diverse fused or bridged ring systems relevant to medicinal chemistry.
• Total Synthesis: Enantiopure seven-membered lactam units appear in the total synthesis of natural products and pharmaceutical intermediates.

The Cbz group is removed by Pd/C-catalyzed hydrogenolysis (H₂, atmospheric pressure, common solvents such as MeOH or EtOH), liberating the free amine for downstream coupling or cyclization steps.

Handling, Storage, and Safety

As with most synthetic organic intermediates containing a carbamate functionality, standard laboratory precautions apply:

• Storage: Store in a cool, dry, well-ventilated area, away from light and moisture. Refrigeration (2–8 °C) is recommended for long-term stability, though specific stability data should be confirmed with Aladdin Scientific's certificate of analysis (CoA).
• Handling: Use appropriate personal protective equipment (PPE) including gloves, lab coat, and eye protection. Work in a fume hood when weighing or dissolving the compound.
• Solvents: The compound is expected to be soluble in common organic solvents such as DCM, DMF, DMSO, EtOAc, and MeOH. Solubility in aqueous systems is likely limited due to the hydrophobic benzyl carbamate moiety.
• Disposal: Dispose of waste according to local environmental regulations for organic chemical waste.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Ordering and Quality Information

Benzyl (S)-(2-oxoazepan-3-yl)carbamate is available from Aladdin Scientific under catalog number B178943. When placing an order, researchers and procurement teams should consider the following:

• Purity: Request the certificate of analysis (CoA) for the specific lot to confirm purity (typically assessed by HPLC or NMR), identity, and chiral purity (ee value).
• Quantity: Available in research quantities; contact Aladdin Scientific for bulk pricing if larger amounts are required.
• Lead Time: Lead time may vary depending on stock availability. Contact Aladdin Scientific's sales team for current stock status.
• Documentation: CoA, SDS, and structural confirmation data (NMR, MS) can be requested at the time of order or download from the product page.

For inquiries, contact Aladdin Scientific customer service through the official website or regional distributors.