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.
To a stirred solution of 4 (2 kg, 8 mol) in CH2Cl2 (2 L) was added oxalyl chloride (1.4 L, 16 mol) dropwise at 0 ¡ãC. The resulting solution was stirred at room temperature for another 4 h and concentrated in vacuo. To a stirred solution of (R)-4-phenyloxazolidin-2-one (1.3 kg, 8 mol) and TEA (1.7 L, 12 mol) in CH2Cl2 (4.8 L) at 0 ¡ãC was added the substituted cinnamic chloride in CH2Cl2 (800 mL) dropwise. The mixture was stirred at 0 ¡ãC for 1 h and then raised to room temperature for 3 h when a saturated solution of NH4Cl (600 mL) was added. The aqueous layer was separated, and the organic solution was washed with water (600 mL .x. 3), brine (800 mL), and dried over Na2SO4. The organic solution was evaporated and 2.9 kg of 5 was obtained after recrystallization in EtOH in 93percent yield, mp 143-145 ¡ãC, (c 1.0, CHCl3). 1H NMR (300 MHz, CDCl3): delta 7.86 (d, J = 15.5 Hz, 1H), 7.75 (d, J = 15.3 Hz, 1H), 7.30-7.50 (m, 11H), 7.23 (m, 2H), 7.03 (dd, J = 2.3, 8.6 Hz, 1H), 5.64 (dd, J = 4.0, 9.0 Hz, 1H), 5.15 (s, 2H), 4.85 (t, J = 8.9 Hz, 1H), 4.36 (dd, J = 3.9, 8.8 Hz, 1H). 13C NMR (100 MHz, CDCl3): delta 164.6, 158.9, 153.7, 146.5, 138.9, 136.5, 135.8, 129.8, 129.2, 129.1, 128.6, 128.5, 128.4, 128.1, 127.6, 127.5, 126.0, 125.9, 121.5, 117.4, 117.1, 114.4, 70.0, 69.9, 57.8. HRMS (ESI): Calcd for C25H21NO4Na: 422.1368. Found: 422.1349., 90319-52-1
90319-52-1 (R)-4-Phenyloxazolidin-2-one 730425, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Article; Zhang, Qiang; Li, Jian-Feng; Tian, Guang-Hui; Zhang, Rong-Xia; Sun, Jin; Suo, Jin; Feng, Xin; Fang, Du; Jiang, Xiang-Rui; Shen, Jing-Shan; Tetrahedron Asymmetry; vol. 23; 8; (2012); p. 577 – 582;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem