Reformation of thalidomide from its hydrolysis compound via intramolecular dehydration

Takuya Taniguchi, Miri Nakamura, Koichi Tsutao, Kohei Otogawa, Yoshiyuki Ogino, Toru Asahi

Research output: Contribution to journalArticlepeer-review

Abstract

Thalidomide, a famous chiral drug, can be hydrolyzed into three different compounds depending on the reaction site of hydrolysis. This work presents the reformation of thalidomide from one of the hydrolysis compounds through an intramolecular dehydration reaction in acetonitrile. The difference of dehydration behavior between hydrolysis compounds was rationalized based on molecular structures: The reformable molecule has the preferable geometric environment for intramolecular dehydration.

Original languageEnglish
Pages (from-to)1388-1391
Number of pages4
JournalChemistry Letters
Volume50
Issue number7
DOIs
Publication statusPublished - 2021 Jul

Keywords

  • Hydrolysis
  • Intramolecular dehydration
  • Thalidomide

ASJC Scopus subject areas

  • Chemistry(all)

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