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Published on: November 23, 2016
Methods for syntheses of N-methyl-DL-aspartic acid derivatives
1Department for Pharmaceutical Chemistry, Semmelweis University, Budapest, Hungary. bormik@hogyes.sote.hu
Amino Acids
|March 6, 2007
Summary
This study presents a novel synthesis for N-methyl-DL-aspartic acid (NMA) and its derivatives. New methods enable efficient preparation of NMA-alpha-amide and NMA diamide, expanding synthetic possibilities.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Amino Acid Chemistry
Background:
- N-methyl-DL-aspartic acid (NMA) is a naturally occurring amino acid.
- Existing synthetic routes for NMA and its derivatives may lack efficiency or practicality.
Purpose of the Study:
- To develop a novel and practical method for synthesizing N-methyl-DL-aspartic acid (NMA).
- To establish new synthetic pathways for various N-methyl-aspartic acid derivatives.
Main Methods:
- Michael addition of methylamine to dimethyl fumarate for NMA synthesis.
- Regioselective transformation of fumaric/maleic acid mono-esters and amides into beta-substituted aspartic acid derivatives.
- Utilized intermediate products like sulphinamide anhydride and aspartic anhydride for efficient NMA-alpha-amide preparation.
Main Results:
- Successfully synthesized NMA via Michael addition.
- Developed regioselective methods for beta-substituted aspartic acid derivatives.
- Achieved efficient synthesis of NMA-alpha-amide and NMA diamide.
- Identified temperature-dependent side reactions leading to diazocinone formation.
Conclusions:
- A practical synthesis for NMA and its derivatives has been established.
- The developed methods offer efficient routes to key NMA intermediates and final products.
- Understanding side reactions is crucial for optimizing synthetic outcomes.
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