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.
Production Example 1 (4R) -3- (4-Azidobutanoyl)4-phenyloxazolidin-2-one A catalytic amount of dimethylformamide was added to a solution of 4-azidobutyric acid (10.3 g, 80.0 mM) in 100 ml of methylene chloride and, thereafter, thionyl chloride (8.7 ml, 119.5 mM) was added dropwise thereto under ice-cooling. After stirring the reaction mixture at room temperature for one hour, it was evaporated to give a crude acid chloride. A 1.6M solution of n-butyl lithium in hexane (40.2 ml, 64.3 mM) was added dropwise into a solution of (4R)-4-phenyl-2-oxazolidinone (manufactured by Aldrich; 10 g, 61.3 mM) in tetrahydrofuran (80 ml) at -78¡ã C. and the mixture was stirred at the same temperature for 30 minutes. A solution of the previously synthesised acid chloride in tetrahydrofuran (100 ml) was slowly added dropwise into the reaction mixture and the mixture was further stirred for 30 minutes. The reaction was ceased by adding dropwise a saturated aqueous solution of sodium bicarbonate into the reaction mixture followed by warming up to room temperature. The mixture was poured into water followed by extracting with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was subjected to a silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (17 g, 99percent). 1H-NMR(CD Cl3) delta:1.84(2H,quint,J=7 Hz), 2.88(2H,t,J=7 Hz), 3.25 (2H,t,J=7 Hz),4.24(1H,dd,J=4.9 Hz), 4.65(1H,t,J=7 Hz), 5.36(1H,dd,J=4.9 Hz), 7.22-7.35(5H,m)., 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; Eisai Co., Ltd.; US6218550; (2001); B1;,
Oxazolidine – Wikipedia
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