Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
[CAS# 114744-83-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• Molecular Formula: C₁₃H₁₈N₂O₄
• Molecular Weight: 266.29
• CAS Registry Number: 114744-83-1
• SMILES: CC(C(=O)N(C)OC)NC(=O)OCc1ccccc1

Properties

• Solubility: Very slightly soluble (0.85 g/L) (25 ºC), Calc.^*
• Density: 1.166±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 87-89 ºC^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

^** Kano, Shinzo; Chemical & Pharmaceutical Bulletin 1988, V36(9), P3296-303.

Discovory and Applicatios

Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate, commonly known as a derivative of carbamate, is an important compound in organic chemistry due to its versatile applications in medicinal chemistry and pharmaceuticals. This compound features a benzyl group attached to a carbamate moiety, which includes a chiral center and a methoxy(methyl)amino group. Its structure provides a valuable framework for the development of biologically active molecules and drug candidates.

The discovery of Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate was motivated by the need for new chemical entities with potential therapeutic applications. The carbamate functional group is well-known for its stability and ability to participate in a variety of chemical reactions. By incorporating a methoxy(methyl)amino group, this compound enhances its utility in drug design, particularly in the development of enzyme inhibitors and receptor modulators. The chiral center at the 2-position is also significant, as it can influence the biological activity and selectivity of the compound.

One notable application of Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate is in the synthesis of inhibitors for various enzymes. For instance, carbamate derivatives are often employed as inhibitors of acetylcholinesterase, an enzyme critical in the nervous system. Inhibiting this enzyme can be beneficial for treating conditions such as Alzheimer's disease, where acetylcholine levels are disrupted. The methoxy(methyl)amino group in the compound allows for fine-tuning of the inhibitor's affinity and selectivity towards acetylcholinesterase, making it a promising candidate for further research in neurodegenerative diseases.

In addition to its role in enzyme inhibition, Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate has been investigated for its potential as a receptor ligand. The compound's structure allows it to interact with various receptors, potentially influencing cellular signaling pathways. By modifying the benzyl and carbamate groups, researchers can design ligands with specific binding affinities and functional activities, which is valuable for developing new drugs targeting a range of receptors involved in different physiological processes.

The synthesis of Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate involves the reaction of benzyl alcohol with a carbamate precursor, followed by the introduction of the methoxy(methyl)amino group. This multi-step synthesis allows for precise control over the compound's stereochemistry and functional groups. The resulting product can be further modified to create analogs with varied biological activities, expanding its potential applications in drug discovery and development.

In the realm of pharmaceuticals, this compound's ability to act as a versatile building block for drug synthesis underscores its significance. Its stability and reactivity make it a valuable tool for researchers seeking to develop new therapeutic agents with improved efficacy and reduced side effects. The exploration of Benzyl [(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate and its derivatives continues to contribute to advancements in medicinal chemistry and the search for novel treatments for various diseases.