Synthesis of N-alkyl-N-methyl amino acids. Scope and limitations of base-induced N-alkylation of Cbz-amino acids

M Stodulski, J Mlynarski

Index: Stodulski, Maciej; Mlynarski, Jacek Tetrahedron Asymmetry, 2008 , vol. 19, # 8 p. 970 - 975

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Citation Number: 16

Abstract

The reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids with NaH/alkyl iodides gave the corresponding N-Cbz-N-alkyl derivatives in good to high yields. The scope and limitations of this simple N-alkylation reaction were investigated as a convenient and flexible attempt to prepare unsymmetrically N, N-diprotected α-amino acids. The procedure is based on the N-alkylation of N-carbamoyl amino acids, a one-pot deprotection/ ...