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Letters in Organic Chemistry

Author(s): Zetryana Puteri Tachrim, Kazuhiro Oida, Fumina Ohashi, Natsumi Kurokawa, Lei Wang, Takeyuki Suzuki and Makoto Hashimoto *

DOI: 10.2174/1570178617666200207111127

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Synthesis of TFA-protected α-Amino Acid Chloride via a Vilsmeier Reagent for Friedel–Crafts Acylation

Page: [645 - 653] Pages: 9

  • * (Excluding Mailing and Handling)

Abstract

α-Amino acid chlorides are reactive coupling agents in amide (peptide) formation. The Vilsmeier reagent ((chloromethylene)dimethylammonium chloride) offers a convenient way to prepare α-amino acid chlorides for peptide synthesis. Its use with N-trifluoracetyl (TFA)-protected isoleucine and allo-isoleucine is described. The 1H-NMR of the α-proton signal offers a convenient way to monitor the chirality retention in the acid chloride forming reaction and subsequent Friedel-Crafts acylation of arenes which result in α-amino acid aryl-ketone with no loss of chirality.

Keywords: Vilsmeier reagent, α-Amino acid chloride, Friedel-Crafts acylation, α-amino acid, α-amino arylketone, racemization.

Graphical Abstract

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