Synthesis of derivatives of ω-isocyanato-α-methylamino, ω-ureido-α-methylamino, and N^α-methyl-α,ω-diamino acids

Abstract:

Homochiral Nα-methyl-2,3-diaminopropionic and Nα-methyl-2,4-diaminobutyric acid derivatives 8a,b were obtained via a stereoconservative four-step synthesis starting from hexafluoroacetone protected L-aspartic and L-glutamic acid 2a,b, respectively. Hexafluoroacetone protected ω-isocyanato-α-methylamino acids 4a,b - the key intermediates of the synthesis - are versatile building blocks for amino acid and peptide modification and promising candidates for combinatorial chemistry. Upon reaction with alcohols, compounds 4 give activated Nω-urethane protected ω-amino-α-methylamino acid derivatives 5-7; upon reaction with amines, ω-ureido-α-methylamino acid derivatives 10-12 and 3-methylamino-pyrrolidin-2-ones 13 are available.

Año de publicación:

2000

Keywords:

• ω-Ureido-α-methylamino acids
• Hexafluoroacetone
• N -Methyl-2,3-diaminopropionic acid derivatives and homologues α
• ω-Isocyanato-α-methylamino acid derivatives
• 3-Methylaminopyrrolidin-2-ones

Fuente:

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