Methyl 2-Acetamido-2-phenylacetate: Properties & Applications

Methyl 2-Acetamido-2-phenylacetate is a protected alpha-amino acid ester that serves as a versatile chiral building block and pharmaceutical intermediate in organic synthesis workflows.

Chemical Name

Methyl 2-Acetamido-2-phenylacetate

SKU

M691420

Functional Class

N-Acetyl alpha-amino acid methyl ester

Key Functional Groups

Acetamide, ester, phenyl

Primary Application

Chiral intermediate in pharmaceutical and peptide synthesis

Storage Recommendation

Store in a cool, dry place away from light and moisture

Chemical Identity and Structure

Methyl 2-Acetamido-2-phenylacetate is an N-acetyl protected derivative of phenylglycine in which the carboxylic acid is esterified as a methyl ester. The molecule features three key functional groups: an acetamide group providing nitrogen protection, a methyl ester enabling downstream hydrolysis or further functionalization, and a phenyl ring that introduces aromatic character and contributes to the compound's chiral centre at the alpha carbon.

This structural motif places the compound firmly within the class of alpha-acetamido esters, a well-recognised family of building blocks used across medicinal chemistry, asymmetric synthesis, and peptide chemistry. The combination of a labile ester and a stable acetamide allows orthogonal deprotection strategies, making it attractive for multi-step synthesis planning.

Synthesis and Preparation Context

Alpha-acetamido esters such as Methyl 2-Acetamido-2-phenylacetate are commonly accessed via acetylation of the corresponding alpha-amino acid ester. Phenylglycine methyl ester, derived from phenylglycine, can be treated with acetic anhydride or acetyl chloride under mild conditions in the presence of a base to furnish the target N-acetyl product in good yield. Alternatively, the Strecker synthesis and related condensation routes offer pathways to the alpha-amino nitrile precursor, which can be hydrolysed and esterified to deliver the title compound.

The methyl ester moiety is readily hydrolysed under basic aqueous conditions, releasing the free N-acetyl amino acid, while the acetamide nitrogen can be deprotected by acidic hydrolysis to unmask the free amine. This orthogonality is a practical advantage in synthetic sequences where selective functional group manipulation is required.

Laboratory and Pharmaceutical Applications

Methyl 2-Acetamido-2-phenylacetate finds utility as an intermediate in the synthesis of biologically active molecules, including peptidomimetics, enzyme inhibitors, and other nitrogen-containing pharmaceuticals. Its phenylglycine backbone is found in several clinically relevant compounds, and the protected form allows controlled incorporation into larger molecular frameworks without unwanted side reactions at the amine.

In asymmetric synthesis, alpha-acetamido acrylate derivatives serve as substrates for asymmetric hydrogenation using chiral transition-metal catalysts, a landmark methodology developed in the context of amino acid synthesis. While the saturated ester described here is the direct product of such hydrogenation, it may also serve as a reference standard or as a starting material for further transformations including reductive amination, acylation, or cyclisation to form oxazolone and related heterocyclic intermediates.

Researchers in agrochemical and materials science contexts may also explore this compound as a model substrate for studying amide bond reactivity and ester hydrolysis kinetics.

Handling, Safety, and Storage Guidelines

As with all laboratory reagents, Methyl 2-Acetamido-2-phenylacetate should be handled in accordance with standard good laboratory practice. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use. General precautions include the use of appropriate personal protective equipment such as gloves, laboratory coat, and eye protection.

The compound should be stored in a cool, dry location away from direct light and sources of moisture to maintain stability and purity over time. Containers should be kept tightly sealed when not in use. Disposal must be carried out in compliance with local regulatory requirements for chemical waste.

Researchers should verify the current SDS for specific hazard classifications, first-aid measures, and regulatory information relevant to their jurisdiction before working with this material.

Ordering Information and Specifications

Methyl 2-Acetamido-2-phenylacetate is available from Aladdin Scientific under SKU M691420. Researchers and procurement teams are encouraged to contact Aladdin Scientific directly for current pricing, available pack sizes, purity specifications, and lead times. Bulk quantities and custom purity grades may be available on request.

For quality assurance, Aladdin Scientific provides product documentation including certificate of analysis (CoA) and SDS. These documents are accessible through the product page or by contacting our technical support team. All products are subject to Aladdin Scientific's standard quality control processes to ensure reproducibility and reliability in your research.

Frequently asked questions

What is Methyl 2-Acetamido-2-phenylacetate used for in research?

Methyl 2-Acetamido-2-phenylacetate is primarily used as a protected alpha-amino acid ester building block in pharmaceutical synthesis, peptidomimetic design, and asymmetric synthesis. Its orthogonally deprotectable amine and ester groups make it well-suited for multi-step synthetic sequences.

How should Methyl 2-Acetamido-2-phenylacetate be stored to maintain stability?

The compound should be stored in a cool, dry location away from direct light and moisture, with containers kept tightly sealed. Always refer to the current Safety Data Sheet from Aladdin Scientific for the most accurate and up-to-date storage recommendations.

Can the methyl ester and acetamide groups in this compound be selectively deprotected?

Yes. The methyl ester is typically hydrolysed under mild basic aqueous conditions, while the acetamide nitrogen requires more forcing acidic hydrolysis conditions for deprotection. This orthogonality enables selective manipulation of each functional group independently during multi-step synthesis.

What is the Aladdin Scientific SKU for Methyl 2-Acetamido-2-phenylacetate?

Methyl 2-Acetamido-2-phenylacetate is available from Aladdin Scientific under SKU M691420. Contact our sales or technical support team for pricing, pack sizes, and availability.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for acetamide and ester chemistry.
2. Knowles, W. S. Asymmetric Hydrogenations (Nobel Lecture). Angewandte Chemie International Edition, 2002. Context for asymmetric hydrogenation of alpha-acetamido acrylates. doi:10.1002/1521-3773(20020104)41:1<1::AID-ANIE10>3.0.CO;2-2
3. Aladdin Scientific. Product Page: Methyl 2-Acetamido-2-phenylacetate, SKU M691420. Aladdin Scientific Co., Ltd.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.