Synthetic Preparation of N-Methyl-alpha-amino Acids
Luigi Aurelio, Robert T. C. Brownlee, and Andrew B. Hughes*
Chem. Rev. 2004, 104, 5823-5846
2.1. Nucleophilic Substitution of alpha-Bromo Acids
Fischer and Mechel prepared N-methylalanine, -leucine, and -phenylalanine by nucleophilic displacement of bromide from optically active (R)-R-bromo acids (Scheme 1).
The R-bromo acids were nucleophilically substituted with excess methylamine at 0 °C, providing NMAs with opposite configuration to the parent amino acids. In this mode, they prepared N-methylalanine, -leucine, and -phenylalanine, all of the L-configuration (Scheme 1).
http://127.0.0.1/Naf1/2009531202642_n-methylation.aminoacid.pdf
Luigi Aurelio, Robert T. C. Brownlee, and Andrew B. Hughes*
Chem. Rev. 2004, 104, 5823-5846
2.1. Nucleophilic Substitution of alpha-Bromo Acids
Fischer and Mechel prepared N-methylalanine, -leucine, and -phenylalanine by nucleophilic displacement of bromide from optically active (R)-R-bromo acids (Scheme 1).
The R-bromo acids were nucleophilically substituted with excess methylamine at 0 °C, providing NMAs with opposite configuration to the parent amino acids. In this mode, they prepared N-methylalanine, -leucine, and -phenylalanine, all of the L-configuration (Scheme 1).
http://127.0.0.1/Naf1/2009531202642_n-methylation.aminoacid.pdf