With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.
To a stirred solution of (S)-4-benzyl-3-propionyl oxazolidin-2-one (30 g, 128.755 mmol) in THF (50 mL), sodium bis(trimethylsilyl)amide (128.7 mL, 128.755 mmol, 1M in THF) was added slowly at -78 C and the mixture was stirred at that temperature for 2h. A solution of 3-iodo-l-propane (64.89 g, 386.265 mmol) was added to the reaction mixture at -78 C and it was stirred for additionally 2h. On completion, the reaction mixture was quenched with saturated NH4CI and extracted twice with EtOAc (2 x 200 mL) . The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, concentrated and the resulting residue was purified by silica gel column chromatography (0-10% EtOAc in pet ether as elute) to afford the title compound as colorless liquid.1H NMR (400MHz, CDCl3) delta = 7.36 – 7.30 (m, 2H), 7.30 – 7.27 (m, 1H), 7.24 – 7.19 (m, 2H), 5.83 (tdd, J = 7.2, 10.0, 17.1 Hz, 1H), 5.17 – 5.00 (m, 2H), 4.75 – 4.61 (m, 1H), 4.28 – 4.07 (m, 2H), 3.94 – 3.80 (m, 1H), 3.29 (dd, J = 3.4, 13.2 Hz, 1H), 2.70 (dd, J = 10.0, 13.5 Hz, 1H), 2.53 (td, J = 6.7, 13.9 Hz, 1H), 2.24 (td, J = 7.0, 13.8 Hz, 1H), 1.19 (d, J = 6.8 Hz, 3H).LCMS: 84% (M + H) 274., 131685-53-5
131685-53-5 (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone 10966403, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Patent; LEO PHARMA A/S; LIANG, Xifu; LARSEN, Jens; (179 pag.)WO2018/108231; (2018); A1;,
Oxazolidine – Wikipedia
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