With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.
(45,5i?)-5-[3,5-w(trifluoromethyl)phenyl]-4-methyl-l,3-oxazolidin-2-one (Intermediate 17, 400 mg, 1.28 mmol) was treated with NaH (60% in oil, 128 mg, 3.2 mmol) and 2-(bromomethyl)-l-iodo-4- (trifluoromethyl)benzene (Intermediate 11, 466 mg, 1,28 mmol). The reaction was stirred at room temperature for 18 h. The reaction was quenched with H2O (1 mL) and partitioned between EtOAc (80 mL) and H2O (25 mL). The aqueous phase was re-extracted with EtOAc (2 x 20 mL) and the combined organic extracts were washed with brine (30 mL), dried (MgStheta4) and concentrated in vacuo to give the crude product. This was purified by flash silica-gel chromatography (0-30% EtOAc in hexanes gradient) to afford (4S’,5i?)-5-[3,5-/5(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3- oxazolidin-2-one as a white solid. LCMS = 598.0 (M+l)+. lH NMR (CDCI3, 500 MHz): delta 8.06 (d, J =8.2 Hz, 1 H)3 7.93 (s, 1 H), 7.82 (s, 2 H), 7.61 (s, 1 H), 7.33 (dd, J= 8.2, 1.4 Hz, 1 H), 5.79 (d, J= 7.8 hz, 1 H), 4.91 (d, J= 16 Hz, 1 H)54.40 (d, J= 16 Hz, 1 H), 4.16-4.06 (m, 1 H), 0.83 (d, J= 6.4 Hz, 3 H).
As the paragraph descriping shows that 875444-08-9 is playing an increasingly important role.
Reference£º
Patent; MERCK & CO., INC.; WO2007/81571; (2007); A2;,
Oxazolidine – Wikipedia
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