(R)-[3-(3-Fluoro-4-morpholinophenyl)-2...

To a solution of 132.8 g of (R)-N-[[3-[3-fluoro-4-morpholinyl]phenyl]-2-oxo-5- oxazolidinyl] methanol and 87.1 g of triethylamine in IL of methylene dichloride at O(R)-[N-3-(3-Fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl methane sulfonate[134] Triethyl amine (68.2g), Methane sulfonyl chloride (48.3g) are added to a flaskcontaining Dichloromethane (1900ml) and(R)-[N-3-(3-Fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methanol (lOOg) at 20-30°C with constant stirring for 2-3 hours. After cooling filtration wash the solid with Dichloromethane followed by water wash dried in air tray dryer. Yield: 1.20.: Percentage 95 w/w.[135]Example-1: Preparation of (5R)-(N)-[[3-fluoro-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl] sulphonate.(5R)-(N)-[3-fluoro-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol (1 mole eq, 100 g) was taken in 600 ml methylene dichloride and cooled to 0-5Example-8: Preparation of (R)-[[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5- oxazolidinyljmethyl] 4-methylmethanesulfonate (IX)(R)-[N-3-(3-fluoro-4-mo holinylphenyl)-2- oxo-5-oxazolidinyl] methanol (6.5 g) and methanesulfonyl chloride (3.78 g) were dissolved in DCM (60 ml). The resulting solution was cooled to 0-5°C and to the cold solution; triethylamine (3.76 g) was added. The obtained solution was warmed to room temperature and stirred for lOh. After the completion of reaction, it was concentrated. In the resulting reaction mass, water (50 ml) was added and stirred at 50-55°C for lh and further at 25-30°C for next lh. The solid obtained was filtered, washed with water and suck dried. The suck dried material was suspended in methanol (65 ml) and heated to 60°C. The suspension was stirred at 55-60°C for 2h and further at room temperature for lh. The solid was filtered, washed with methanol at room temperature and dried to obtain the titled compound (6 g) with 73percent yield.ExampIe-3: (R)-fN-f3-(3-fluoro-4-morphoIinylphenylV-2-oxo-5- oxazolidinyll methyl] methane sulfonateTo a solution of 100 g of N-carbobenzyloxy-3-fluoro-4-morpholinyl aniline in 500 mL of freshly distilled tetrahydrofuran at -80°C under nitrogen, was added 105 mL of n-butyl lithium/hexane via syringe within 90 minutes, and the mixture stirred for 60 minutes. Further, a solution of 45.9 g of (R)-glycidylbutyrate in 80 mL of tetrahydrofuran was added within 90 minutes, and stirred for 60 minutes. The reaction mixture was removed from the dry ice bath, and allowed to come to ambient temperature. After stirring for 4-6 hours, the reaction mixture was quenched in 134 g of saturated aqueous ammonium chloride solution, followed by 500 mL of toluene, and the aqueous layer extracted with toluene. The combined organic layers were washed with 360 mL of brine. The organic layer was treated with 4 g activated charcoal and stirred for 30 minute and filtered. The filtrate was concentrated under vacuum at 60°C to remove toluene completely. In the mixture of residue of (R)-N-[[3-[3-fluoro-4- moφholinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol, 300 mL methylene dichloride and 46 g triethylamine mixture was added within 90 minutes. The reaction mixture was warmed to 45°C and stirred for 3 hours. Methylene dichloride was removed under vacuum below 50°C and the residue was cooled to room temperature. The residue were triturated with 500 mL of toluene and stirred for 1 hour and filtered. The wet-cake was washed with toluene and slurried in water for 1 hour. The solid was filtered and washed with water. The product dried at 60°C to 65°C to get 95 g (84percent) of (R)-[N-[3-(3- fluoro-4-mo holinylphenyl)-2-oxo-5-oxazolidinyl]methyl]methane sulfonate.(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol (50 gr) and triethylamine (42.6 gr) in methylene dichloride (250 ml) was cooled in ice-bath and treated with methane sulphonyl chloride (38.2 gr). III.

Molecular Weight:374.4
XLogP3:0.8
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:374.09478567
Monoisotopic Mass:374.09478567
Topological Polar Surface Area:93.8
Heavy Atom Count:25
Complexity:577
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes