Analyzing the synthesis route of 108149-63-9

108149-63-9, The synthetic route of 108149-63-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108149-63-9,(R)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate,as a common compound, the synthetic route is as follows.

To a mixture of 40 (500 mg; 1.14 mmol), 1,1-dimethylethyl (4R)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylate [49](343 mg; 1.48 mmol), and triphenylphosphine (388 mg;1.48 mmol) in THF (10 mL) was added diisopropyl azidodicarboxylate(300 mL; 1.5 mmol) in a dropwise fashion. After stirring atroom temperature overnight, the reaction was concentrated underreduced pressure and the resultant residue was purified by silicagel chromatography eluting with (0-30%). The solid thus obtainedwas washed with MeOH, then dissolved in DCM (5 mL) and treatedwith TFA (5 mL). After 2 h, the reaction was concentrated underreduced pressure and the residue was dissolved in DCM, washedwith aq. NaHCO3, dried (Na2SO4) and concentrated. The solid thatwas obtained was dissolved in a minimal amount of THF andtreated with excess HCl/ether. The resultant precipitatewas filteredto afford the hydrochloride salt of 44 (300 mg, 48%) as a pale yellowsolid. 1H NMR (400 MHz, CDCl3, free base) delta 8.22 (s, 1H), 8.04 (s, 1H),7.97 (s, 1H), 7.71 (d, J 1.96 Hz, 1H), 7.47e7.54 (m, 1H), 7.30e7.39(m, 2H), 6.68 (d, J 8.61 Hz, 1H), 5.79 (s, 2H), 3.83 (d, J 6.26 Hz,2H), 3.42e3.60 (m, 2H), 3.20 (t, J 4.89 Hz, 1H), 2.17 (s, 1H), 2.01 (s,2H). LCMS (APCI) m/z: mass calcd. for C22H18ClF3N4O3S: 510.07,found: 511.2 [(M+H)+].

108149-63-9, The synthetic route of 108149-63-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Patch, Raymond J.; Huang, Hui; Patel, Sharmila; Cheung, Wing; Xu, Guozhang; Zhao, Bao-Ping; Beauchamp, Derek A.; Rentzeperis, Dionisios; Geisler, John G.; Askari, Hossein B.; Liu, Jianying; Kasturi, Jyotsna; Towers, Meghan; Gaul, Micheal D.; Player, Mark R.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 830 – 853;,
Oxazolidine – Wikipedia
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