Synthesis of TFA-protected α-Amino Acid Chloride via a Vilsmeier Reagent for Friedel–Crafts Acylation-Reference-Cited by-同舟云学术

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

Published:2020-08-18 Issue:8 Volume:17 Page:645-653
ISSN:1570-1786
Container-title:Letters in Organic Chemistry
language:en
Short-container-title:LOC

Author:

Tachrim Zetryana Puteri¹,Oida Kazuhiro¹,Ohashi Fumina¹,Kurokawa Natsumi¹,Wang Lei²,Suzuki Takeyuki³,Hashimoto Makoto¹

Affiliation:

1. Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 0608589, Japan

2. Department of Pharmacy, School of Chemical Engineering, Dalian University of Technology, Dalian 116023, China

3. Division of Applied Science, The Institute of Scientific and Industrial Research, Osaka University, Osaka 5670047, Japan

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.

Funder

Ministry of Education, Science, Sports, and Culture Grant-in-Aid for Scientific Research

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry,Biochemistry

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