Synthesis of Lacosamide (Vimpat) and Its Derivatives from Aziridine-(2R)- carboxylate

被引：13

作者：

Jeong, Hyeonsu ^{[1
]}

Yadav, Nagendra Nath ^{[2
]}

Ha, Hyun-Joon ^{[1
]}

机构：

[1] Hankuk Univ Foreign Studies, Dept Chem, Yongin 17035, Kyunggi Do, South Korea

[2] North Eastern Reg Inst Sci & Technol, Dept Chem, Nirjuli 791109, Arunachal Prade, India

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 06期

关键词：

(R)-lacosamide; Vimpat; antiepileptic drug; aziridine regioselectivity; ASYMMETRIC-SYNTHESIS; ANTICONVULSANT ACTIVITIES; EFFICIENT SYNTHESIS; AMINO-ACID; SUBSTITUTION; ALKALOIDS; ANALOGS; AGENTS; IONS;

D O I：

10.1055/s-0036-1588093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and scalable synthesis of the antiepileptic drug (R)-lacosamide and its derivatives has been achieved from commercially available aziridine-(2R)-carboxylate in three simple sequential steps, including regioselective aziridine ring opening, debenzylation followed by acetylation in one pot, and amide formation. The advantage of this protocol is that the starting material and reagents are commercially available and a single purification by recrystallization is required after all the chemical transformations, providing the final drug in >99.9% ee.

引用

页码：1264 / 1272

页数：9

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