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

[ Vol. 17 , Issue. 8 ]

Author(s):

Zetryana Puteri Tachrim, Kazuhiro Oida, Fumina Ohashi, Natsumi Kurokawa, Lei Wang, Takeyuki Suzuki and Makoto Hashimoto *   Pages 645 - 653 ( 9 )

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.

Affiliation:

Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 0608589, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 0608589, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 0608589, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 0608589, Department of Pharmacy, School of Chemical Engineering, Dalian University of Technology, Dalian 116023, Division of Applied Science, The Institute of Scientific and Industrial Research, Osaka University, Osaka 5670047, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 0608589

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