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Synthesis of (–)‐Oseltamivir by Using a Microreactor in the Curtius Rearrangement
Author(s) -
Ishikawa Hayato,
Bondzic Bojan P.,
Hayashi Yujiro
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100074
Subject(s) - curtius rearrangement , chemistry , isocyanate , azide , trimethylsilyl azide , acetamide , nucleophile , combinatorial chemistry , microreactor , organic chemistry , catalysis , polyurethane
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 large‐scale 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.