(5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxa

119 g (367 mmol) of Compound XXIX was dissolved in 300 mL of tetrahydrofuran/150 mL of dimethylformamide, 38.19 g (477 mmol) of lithium-t butoxide was slowly added dropwise thereto at 0°C, the resulting solution was stirred for 10 minutes, 63 mL (440 mmol) of (R)-glycidyl butyrate and 21 mL (550 mmol) of methanol were added thereto, and the resultant solution was stirred at room temperature for 3 hours. Subsequently, pH of the reaction mixture was adjusted to approximately 6 using an aqueous ammonium chloride solution and then the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in 1000 mL of 80percent ethylacetate/hexane, was sequentially washed with water and an aqueous saturated sodium chloride solution (brine), and then dehydrated using anhydrous sodium sulfate, followed by concentration under reduced pressure and column chromatography, to obtain 93 g (320 mmol) of Compound B-I as a white solid (yield: 87percent). [0162] Preparation of Compound B-I 119 g (367 mmol) of Compound XXIX was dissolved in 300 mL of tetrahydrofuran/150 mL of dimethylformamide, 38.19 g (477 mmol) of lithium-t butoxide was slowly added dropwise thereto at 0° C., the resulting solution was stirred for 10 minutes, 63 mL (440 mmol) of (R)-glycidyl butyrate and 21 mL (550 mmol) of methanol were added thereto, and the resultant solution was stirred at room temperature for 3 hours. Subsequently, pH of the reaction mixture was adjusted to approximately 6 using an aqueous ammonium chloride solution and then the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in 1000 mL of 80percent ethylacetate/hexane, was sequentially washed with water and an aqueous saturated sodium chloride solution (brine), and then dehydrated using anhydrous sodium sulfate, followed by concentration under reduced pressure and column chromatography, to obtain 93 g (320 mmol) of Compound B-I as a white solid (yield: 87percent). [0174] Butyl lithium (2.3M in n-hexanes, 118.3 ml, 0.272 mol, 1.06 eq) was added at -30° C. to anhydrous tert-butanol (25.0 g, 0.53 mol, 2.07 eq) in anhydrous THF (170 ml), under nitrogen. General procedure: Compound 2 (2 mmol) was dissolved in anhydrous THF (10 mL) then cooled to -78 C under nitrogen followed by slow addition of 1M LHMDS in THF solution (1.7 mL, 1.7 mmol) over 20 min. The resulting mixture was subsequently stirred at -78° C for 1 h before (R)-(-)-glycidyl butyrate (0.24 g, 1.7 mmol) was added drop wise at -78° C and the mixture was stirred at this temperature for 1 h then allowed to gradually warm to room temperature under stirring for 12 hrs. The reaction was quenched with DDW (10 mL) followed by EtOAc (4 mL). Then the two layers were separated and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (3×5 mL), dried over Na3.4.la (2.5 g, 7.7 mmol, 1.0 equiv) was dissolved in THE (20 mL) and cooled to -78°C. n-BuLi (2.5M in hexane) (0.59 g, 9.3 mmol, 1.2 equiv) was gradually added and the reaction mixture was stirred at -78 °C for 1 hour. (R)-oxiran-2-ylmethyl butyrate (1 .33 g, 9.3 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (80-100 percent EtOAc in Hexane) to afford product 3.4.lb which was carry forwarded for next step. (1.46 g, 65percent yield). LCMS (mlz): 292.1 [M+H].(4) Benzyl 4-bromo-3-fluorophenylcarbamate (20 g, 61.7 mmol) was dissolved in 180 mL THF, cooled to -78° C., and LiHMDS (1.0M in THY, 62.4 mL, 62.4 mmol) was added dropwise within 45 min. Will be 30 grams(R) -3- (3-fluorophenyl) -2-oxo-5-oxazolidinylmethanolDissolved in 300 ml of acetonitrile, And will be 46 gramsSilver trifluoroacetate(CF3COOAg) and 30.5 g of BrCl were added to the solution, After stirring at room temperature for 1 day, water was added to the solution and extracted with ethyl acetate. The resulting organic layer was separated and washed with brine and dehydrated. The residue was then filtered, concentrated in vacuo and dried, yielding 37.8 g of the title compound in 92percent yield.

Molecular Weight:290.09
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:288.97498
Monoisotopic Mass:288.97498
Topological Polar Surface Area:49.8
Heavy Atom Count:16
Complexity:279
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes