Synthesis of (-)-Oseltamivir by Using a Microreactor in the Curtius Rearrangement

被引：46

作者：

Ishikawa, Hayato ^{[1
]}

Bondzic, Bojan P. ^{[1
]}

Hayashi, Yujiro ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 30期

关键词：

Tamiflu; Antiviral agents; Total synthesis; Process chemistry; Synthesis design; OSELTAMIVIR PHOSPHATE TAMIFLU; HIGH-YIELDING SYNTHESIS; AZIDE-FREE SYNTHESIS; INHIBITOR OSELTAMIVIR; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; CHEMOENZYMATIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; PRACTICAL SYNTHESIS; FLASH CHEMISTRY;

D O I：

10.1002/ejoc.201100074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A microflow reaction of the Curtius rearrangement by using trimethylsilyl azide as an azide source, followed by trapping of the generated isocyanate with a nucleophile was established, which is safe, inexpensive, and suitable for largescale synthesis. By this flow reaction in the Curtius rearrangement and recrystallization of the late-stage acetamide intermediate the third-generation synthesis of (-)-Oseltamivir has been established, which is efficient, practical, and safe.

引用

页码：6020 / 6031

页数：12

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