A practical one-pot synthesis of dehydroalanine esters

Qingyuan Shi; Mengxiao Zhu; Zhenchu Liang; Xu Dong; Minyue Zhang; Lili Yang; Pingping Sun; Chuanyi Xing; Xiaohao Zha; Fei Li; Hongliang He; Dongyin Chen

doi:10.1039/D5RA00035A

A practical one-pot synthesis of dehydroalanine esters†

Qingyuan Shi,‡^a Mengxiao Zhu,‡^a Zhenchu Liang,‡^a Xu Dong,^a Minyue Zhang,^a Lili Yang,^a Pingping Sun,^a Chuanyi Xing,^a Xiaohao Zha,^a Fei Li,*^abc Hongliang He*^d and Dongyin Chen

*^abce

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* Corresponding authors

^a Medical Basic Research Innovation Center for Cardiovascular and Cerebrovascular Diseases, Ministry of Education, International Joint Laboratory for Drug Target of Critical Illnesses, School of Pharmacy, Nanjing Medical University, Nanjing 211166, China
E-mail: chendongyin@njmu.edu.cn, kldlf@njmu.edu.cn

^b Innovation Center of Suzhou Nanjing Medical University, Suzhou 215000, China

^c National Center of Technology Innovation for Biopharmaceuticals, Suzhou 215000, China

^d Department of Pharmacy, Sir Run Run Hospital, Nanjing Medical University, Nanjing 211100, China
E-mail: hcm1004@163.com

^e The Affiliated Huaian No.1 People's Hospital of Nanjing Medical University, Northern Jiangsu Institute of Clinical Medicine, Huaian 223300, China

Abstract

A practical one-pot synthesis of various dehydroalanine esters was realized via a Cs₂CO₃-mediated simultaneous esterification/elimination process, starting from commercially available N-protected serines and various haloalkanes. This protocol provided easy access to structurally diverse dehydroalanine-based building blocks, which were successfully applied to construct more complex dehydroalanine derived molecules.

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A practical one-pot synthesis of dehydroalanine esters†

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A practical one-pot synthesis of dehydroalanine esters

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