With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.
Synthesis of (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one:To a solution of (R)-4-phenyloxazolidin-2-one (8.30 g, 50.9 mmol) in anhydrous THF (80 mL) were added LiCI (2.48 g, 58.5 mmol) and triethylamine (10.30 g, 101.8 mmol). The resulting solution was stirred at RT for 20 minutes, and was then cooled by an ice- water bath. DMAP (0.63 g, 5.1 mmol) was added followed by drop-wise addition of (E)- but-2-enoyl chloride (6.11 g, 58.5 mmol). The resulting yellow suspension was stirred at 0 ¡ãC for 0.5 h, then at RT for 16 h. Water (160 mL) was added to quench the reaction, and the mixture was extracted with EtOAc (1 x 150 mL, 2 x 100 mL). The combined organic phases were washed with brine (50 mL), dried over magnesium sulfate. The solvent was removed under reduced pressure to give crude product as yellowish oily wax, which was purified by chromatography (0 – 50percent EtO Ac/heptane) to obtain (R,E)-3-but- 2-enoyl-4-phenyloxazolidin-2-one as light yellow wax (8.0 g, 68percent). 1H NMR (300 MHz, CDCI3/TMS): delta 7.50-7.20 (m, 6H), 7.18-7.00 (m, 1H), 5.48 (dd, 1H, J = 8.7, 3.9 Hz), 4.69 (t, 1H, J= 8.7 Hz), 4.27 (dd, 1H, J= 8.7, 3.9 Hz), 1.93 (dd, 3H, J= 6.7, 1.3 Hz); 13C NMR (75 MHz, CDCI3/TMS): delta 164.2, 153.5, 146.9, 138.9, 128.9, 128.3, 125.7, 121.5, 69.8, 57.6, 18.5., 90319-52-1
As the paragraph descriping shows that 90319-52-1 is playing an increasingly important role.
Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Oxazolidine – Wikipedia
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