Uses
Thiomorpholine 1,1-Dioxide is a useful building block, used in the synthetic preparation of antibacterial biaryloxazolidinone analogues, and isothiazolo-pyridine derivatives for use as cyclin G-associated kinase inhibitors and antiviral agents.
Synthesis
To a solution of tert-butylthiomorpholine-4-carboxylate (5.8 g, 0.024 mol) in dichloromethane (50 ml) was added trifluoroacetic acid (70 ml), and the resulting mixture was stirred at 25°C. 5 hours until TLC showed the reaction was complete. Concentrate under reduced pressure to obtain a mixture. Water (30 mL) was added to the mixture, the mixture was basified to pH=8.0 with aqueous ammonia solution, and the mixture was extracted three times with dichloromethane (50 mLx3). The organic extracts were combined and washed with water and brine. The organic extract was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to obtain Thiomorpholine 1,1-dioxide.
References
[1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 247 - 258
[2] Patent: US2006/100426, 2006, A1. Location in patent: Page/Page column 17
[3] Patent: US2006/135764, 2006, A1. Location in patent: Page/Page column 21
[4] Patent: US2006/100236, 2006, A1. Location in patent: Page/Page column 19
[5] Patent: US2006/199839, 2006, A1. Location in patent: Page/Page column 21
