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 solution of Preparation 4H (1.4 g, 4.8 mmol) in THF (15 mL) was added NEt3 (1.3 mL, 9.6 mmol). The reaction mixture was cooled to 0 ¡ãC and trimethylacetyl chloride (0.7 13 mL, 5.8 mmol) was added dropwise and the resulting solution stirred for 30 mm at 0 ¡ãC. In a separate flask, (R)-4-phenyloxazolidin-2-one (3, 1.01 g, 6.24 mmol) in THF (45 mL) at 0 ¡ãC was treated with 1 M LiHMDS solution in THF (dropwise addition of 6.24 mL, 6.24 mmol) and stirred at 0¡ãC. The lithiate was added via cannula to the first flask. The reaction mixture was allowed to warm to rt and was stirred for 3 hours. LC/MS indicated the complete consumption of the starting carboxylic acid and formation of the desired imide. The reaction mixture was poured onto saturated aqueous ammonium chloride (50 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organic extracts were dried over anhydrous sodium sulfate and chromatographed on silica using EtOAc/Hexanes 0 to 100percent 0 + 1gradient to give Preparation 41 as a white foam in 83/0 yield. m/z (M+H) = 433.3. H-NMR (400MHz; CDC13): oe 8.80 (d, J= 4.5 Hz, 1H), 8.11 (dd, J= 9.1, 5.7 Hz, 1H), 7.63 (dd, J 10.5, 2.5Hz, 1H), 7.48-7.43 (m, 1H), 7.40-7.30 (m, 6H), 5.47-5.44 (m, 1H), 4.71 (t, J 8.9 Hz, 1H), 4.31-4.28 (m, 1H), 3.20-3.11 (m, 3H), 2.49-2.46 (m, 1H), 1.82-1.67 (m, 6H)., 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
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Emily, Charlotte; SHAN, Weifang; ZHANG, Liping; WILLIAMS, David, K.; GUO, Weiwei; HUANG, Audris; BALOG, James, Aaron; (72 pag.)WO2017/192844; (2017); A1;,
Oxazolidine – Wikipedia
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