With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.
42 g (165 mmol) compound Formula IV, product of Example 1 was solved in 340 ml water- free terahydrofurane, and the vessel was rinsed by dry N2 gas. The solution was cooled to – 200C, and 55 ml (390 mmol) triethyl-amine was added. A mixture of 40 ml tetrahydrofurane and 20.2 ml pivaloyl chloride (19,8 g, 164 mmol) is added trough a drip-funnel for some 30 min at a temperature between -100C and -20 0C. The precipitate-containing mixture was stirred for 2 h at a temperature between -10 and -200C, and then 24,45 g (150 mmol) solid S (+)-4-phenyl-2-oxazolidinone (Va) and 7,5 g (177 mmol) water-free litium-chloride was sprinkled consecutively into it. Then the suspension was stirred for 4 h while it warmed up to 20-25 0C.The reaction was analytically controlled by thin-layer chromatography. When the spot of S (+)-4-phenyl-2-oxazolidinone decreased to 3%, the reaction was stopped with adding 300 ml toluene and 150 ml saturated ammonium-chloride solution. The phases were separated then the aqueous phase was extracted by 50 ml toluene. The united toluenic solution is washed by 2×150 ml 10% citric acid solution, 2×150 ml IM NaOH solution and at last with 3x 150 ml water. The organic phase was dried on anhydrous Na2SO4, the desiccant was filtered out, and the filtrate was evaporated in vacuum. The residue was crystallized at O0C with 150 ml isopropyl-alcohol. The product (Via) was dried in vacuum in the presence of P2O5. Yield: 55.7 g (93%) Melting point: 100-1020C[alpha]jf =+54.3, (c=l, dichloromethane)1H NMR data: (500 MHz, OMSO-d6, 25 0C) delta 1.42-1.56 (m, 2H), 1.76-1.85 (m, 2H), 2.80 (dt, J = 17.2, 7.5 Hz, IH), 2.90 (dt, / = 17.2, 7.5 Hz, IH), 3.61-3.71 (m, 2H), 3.89-3.99 (m, 2H), 4.13 (dd, J = 8.7, 3.6 Hz, IH), 4.71 (t, J = 8.7 Hz, IH), 5.43 (dd, J – 8.7, 3.6 Hz, IH), 7.12-7.19 (m, 2H), 7.23-7.28 (m, 2H), 7.29-7.34 (m, IH), 7.34-7.42 (m, 4H) ppm., 99395-88-7
99395-88-7 (S)-4-Phenyloxazolidin-2-one 730424, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Patent; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2007/72088; (2007); A1;,
Oxazolidine – Wikipedia
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