875444-08-9, (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
875444-08-9, The chiral intermediate (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one (compound 11 in Scheme 3, prepared by procedure of WO 2007/005572) (28.0 g) is dissolved in DMF (300 mL) and cooled to – 15C. 2 M NaHMDS (39.2 mL, 1.05 eq) was then added over 1 h, followed by addition of the biaryl chloride 7 (Scheme 3) (28.0 g) in DMF (50 mL), maintaining the internal temperature below -10 C. The mixture was warmed to + 12 C and was aged until complete conversion took place. Then 5M HCl (35 mL) was added, followed by 160 mL of 10% IPAC/Heptanes and 340 mL of water, keeping the temperature between 10C and 20C throughout. The layers were cut and the organic layer was washed twice with 150 mL of 1/1 DMF/water followed by two 140 mL waterwashes. The organic layer was then removed under reduced pressure and the resulting residue was purified by flash chromatography (EtOAc/hexanes) to remove the excess oxazolidinone 11 (Scheme 3). The obtained colorless oil was then dissolved in refluxing heptanes (200 mL) and the solution was slowly cooled to -20 C. The resulting slurry was then stirred at -20 C for 2 hours and filtered. The filter cake was washed with cold heptanes and was then dried, yielding 44.0 g (88%) of the desired product of Formula IX (anacetrapib) as an amorphous material. The impurity (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((5′-ethyl-4′-fluoro-2′-methoxy-4-(trifluoromethyl) biphenyl-2-yl)methyl)-4-methyloxazolidin-2-one (DMAP) (?3%), which is formed from 2′-(chloromethyl)-5-ethyl-4-fluoro-2-methoxy-4′-(trifluoromethyl)biphenyl (EBFCI) present in the starting material under the conditions described in Step 7, was detected in the product.
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; LEK Pharmaceuticals d.d.; EP2468735; (2012); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem