Efficient Synthesis of 3-R-Boc-amino-4-(2,4,5-trifluorophenyl)butyric Acid

Abstract

3-R-Boc-amino-4-(2,4,5-trifluorophenyl)butyric acid (9) was obtained from L-methionine in six steps with a total yield of 32%. The α-amino acid segment of L-methionine was transferred to chiral aziridine by amino protection, reduction, hydroxyl derivation, and cyclization. After ring opening of 2,4,5-trifluoro-phenyl magnesium bromide, the methylthiomethyl group was then hydrolyzed to β-amino alcohol and oxidized to the target β-amino acid.

GRAPHICAL ABSTRACT

Keywords:

• β-Amino acid
• aziridine
• Grignard reaction
• hydrolyze
• methylthiomethyl

SUPPORTING INFORMATION

Full experimental details, ¹H HNMR, and high-performance liquid chromatographic spectra of compound 9 can be accessed on the publisher’s website.