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.
Step 4. (R, ?)-4-Phenyl-3-(3-(2,2- -4-yl)acryloyl)oxazolidin-2-one To the solution of (is)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)acrylic acid (9 g, 48.9 mmol) in 350 ml of THF was added TEA (7.49 mL, 53.7 mmol) and the resulting solution was stirred under 2 atmosphere and cooled to -10¡ãC (ice/salt water bath). Piv-Cl (6.37 mL, 51.8 mmol) was then added dropwise via syringe over 5 minutes, a thick precipitate formed, this resulting suspension (A) was stirred at -10¡ãC for 15 min then cooled to -78¡ãC. (R)-4-phenyloxazolidin-2- one (9.01 g, 55.2 mmol) was charged to a separate 500 mL round bottom flask and was dissolved in THF (150 mL) and the resulting solution was stirred and cooled to -78¡ãC under 2 atmosphere. n-BuLi (20.52 mL of a 2.5 M solution in hexane) was then added dropwise via syringe over 5 minutes, to which a precipitate formed and this resulting suspension (B) was stirred at -78¡ãC for 10 min. Then solution A (cooled at -78¡ãC) was then added to solution B via cannula over about 5 minutes. The resulting mixture was then stirred at -78¡ãC for 10 minutes and then the cooling bath was removed and the mixture was stirred for 1.5 h while it gradually warmed up to room temperature. The reaction mixture was poured into a 1000 mL Erlenmeyer flask and was diluted with EtOAc (400mL). This solution was then extracted with water (2 x 300 mL) and washed by brine (300 mL), then dried over sodium sulfate, filtered, and stripped in vacuo to give a clear oil. The oil was taken up in DCM and purified via Biotage (RediSep 220 g silica gel) eluting with a gradient of 0-60percent ethyl acetate in hexane. The tubes containing the product were collected and the solvent removed under reduced pressure to afford the product as a white solid (10.12 g, 62.9percent). MS: m/z = 330 (M+H+)., 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; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BENNETT, David, J.; BUNGARD, Christopher, J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael, P.; HOLLOWAY, M. Katherine; KEERTIKAR, Kartik, M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; MORRIELLO, Gregori, J.; SHEN, Dong-Ming; SHERER, Edward, C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine, M.; ZORN, Nicolas; SATYANARAYANA, Tummanapalli; VIJAYASARADHI, Sivalenka; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/17393; (2015); A2;,
Oxazolidine – Wikipedia
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