Photo-On-Demand Synthesis of α-Amino Acid N-Carboxyanhydrides with Chloroform

Toshiyuki Sugimoto; Tomoya Kuwahara; Fengying Liang; Huirong Wang; Akihiko Tsuda

doi:10.1021/acsomega.2c05299

Photo-On-Demand Synthesis of α-Amino Acid N-Carboxyanhydrides with Chloroform

ACS Omega. 2022 Oct 19;7(43):39250-39257. doi: 10.1021/acsomega.2c05299. eCollection 2022 Nov 1.

Authors

Toshiyuki Sugimoto¹, Tomoya Kuwahara¹, Fengying Liang¹, Huirong Wang¹, Akihiko Tsuda¹

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan.

Abstract

Amino acid N-carboxyanhydrides (NCAs) are conventionally synthesized from α-amino acids and phosgene. The present study reports in situ photo-on-demand phosgenation reactions of amino acids with CHCl₃ for synthesizing NCAs. A series of NCAs were obtained on a gram scale upon photo-irradiation of a mixture solution of CHCl₃ and CH₃CN containing an amino acid at 60-70 °C under O₂ bubbling. This method presents a safe and convenient reaction controlled by light without special apparatuses and reagents.