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

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

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 8 , 2020


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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.

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Article Details

VOLUME: 17
ISSUE: 8
Year: 2020
Published on: 18 August, 2020
Page: [645 - 653]
Pages: 9
DOI: 10.2174/1570178617666200207111127
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