875444-08-9,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.
N-Chlorosuccinimide (10.4 g, 78.1 mmol) was added to a stirred solution of acetaldoxine (3.55 g, 60.1 mrnol) in dry DMF at 00C under N2. The reaction was allowed to warm to room temperature and was stirred for 3 h. Water (100 rnL) was added and the mixture was extracted with Et2O (4 x 80 rnL). The combined extracts were washed with water (50 rnL) and brine (50 mL), dried (Na2SO4) and concentrated in vacuo to afford N-hydroxyethanimidoyl chloride, as a colorless oil. 1H NuMR (500 MHz, CDCl3): delta 8.96 (br s, IH), 2.26 (s, 3 H).Triethylamine (123.4 mg, 170 muL, 1.21 mmol) was added to a stirred solution of (4,S,5.R)-5-[3,5- bis(trifluoromethyl)phenyl]-3-[3-(4-fluoro-5-isopropyl-2-methoxyphenyl)prop-2-yn-l-yl]-4-methyl-l,3- oxazolidin-2-one (21.9 mg, 0.0423 mmol) and N-hydroxyethanimidoyl chloride (124.4 mg, 1.33 mmol) in dry toluene (2 mL) at room temperature under N2. The reaction was heated at reflux for 2 days. The reaction mixture was cooled to room temperature, diluted with IN HCl and extracted with EtOAc (3 x 20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12 x 160 mm, 0-30% EtOAc in hexanes gradient) to afford (45,5Lambda)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3- methylisoxazol-4-yl]methyl}-4-methyl-l,3-oxazolidin-2-one. ^= 0.38 (20% EtOAc/hexanes). LCMS calc. = 575.2; found = 575.3 (M+l)+. 1H NMR (600 MHz, CDCl3): delta 7.84 (s, 1 H); 7.64 (s, 2 H); 7.31 (d, J= 8.3 Hz, 1 H); 6.68 (d, J= 11.8 Hz, 1 H); 5.27 (d, J= 8.0 Hz, 1 H); 4.78 (d, J= 15.6 Hz, 1 H);4.00 (d, J= 15.6 Hz, 1 H); 3.82 (s, 3 H); 3.72-3.68 (m, 1 H); 3.22-3.16 (m, 1 H); 2.38 (s, 3 H); 1.24 (d, J= 7.0 Hz, 3 H); 1.22 (d, J = 7.0 Hz, 3 H); 0.42 (d, J= 6.6 Hz, 3 H).
875444-08-9 (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one 23583229, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Patent; MERCK & CO., INC.; WO2007/81569; (2007); A2;,
Oxazolidine – Wikipedia
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