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Usage

Uses

Used in Organic Synthesis:
D-Alanine, N-methyl-, methyl ester (9CI) is utilized as a key intermediate in organic synthesis for the creation of a variety of biologically active molecules. Its unique structural properties facilitate the development of new chemical entities with potential therapeutic or commercial value.
Used in Drug Discovery Research:
In drug discovery research, D-Alanine, N-methyl-, methyl ester (9CI) is employed as a valuable precursor, enabling the exploration and synthesis of novel drug candidates. Its role in this process is crucial for advancing potential treatments and pharmaceutical innovations.
Used as a Chiral Intermediate in Pharmaceutical Production:
D-Alanine, N-methyl-, methyl ester (9CI) is leveraged as a chiral intermediate in the production of pharmaceuticals. Its stereochemistry is essential for the synthesis of enantiomerically pure compounds, which is critical for ensuring the desired biological activity and minimizing adverse effects.
Used as a Chiral Intermediate in Agrochemicals:
Similarly, in the agrochemical industry, D-Alanine, N-methyl-, methyl ester (9CI) is harnessed as a chiral intermediate. This allows for the development of more effective and targeted agrochemicals with reduced environmental impact.
Used in the Development of Novel Materials and Catalysts:
Due to its unique structural properties, D-Alanine, N-methyl-, methyl ester (9CI) is also used in the research and development of new materials and catalysts. Its potential in this area is significant for creating innovative solutions that address current challenges in various industries.

Upstream product

• 67-56-1 methanol 
• 3913-67-5 N-methylalanine 
• 610800-49-2 (R)-2-[Methyl-(4-nitro-benzenesulfonyl)-amino]-propionic acid methyl ester 

Relevant academic research and scientific papers

Lewis acid catalysed methylation of N-(9H-fluoren-9-yl)methanesulfonyl (Fms) protected lipophilic α-amino acid methyl esters

This work reports an efficient Lewis acid catalysed N-methylation procedure of lipophilic α-amino acid methyl esters in solution phase. The developed methodology involves the use of the reagent system AlCl3/diazomethane as methylating agent and α-amino acid methyl esters protected on the amino function with the (9H-fluoren-9-yl)methanesulfonyl (Fms) group. The removal of Fms protecting group is achieved under the same conditions to those used for Fmoc removal. Thus the Fms group can be interchangeable with the Fmoc group in the synthesis of N-methylated peptides using standard Fmoc-based strategies. Finally, the absence of racemization during the methylation reaction and the removal of Fms group were demonstrated by synthesising a pair of diastereomeric dipeptides.

"One-pot" methylation of N-nosyl-α-amino acid methyl esters with diazomethane and their coupling to prepare N-methyl dipeptides

N-Nosyl-α-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoe amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by 1H NMR and HPLC.

Synthesis and use of 2H-azirin-3-amines as dipeptide synthons

The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx=alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.