3-phenyl-1,3-oxazolidin-2-one

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2, chlorosulfonic acid (1.5 g, 12.87 mmol) was diluted in CCl4 (2 mL) and cooled to 0° C. Then 3-phenyl-1,3-oxazolidin-2-one (280 mg, 1.72 mmol) was diluted in CCl4 (2 mL) and added slowly to the reaction mixture. The reaction mixture was stirred for two hours at 0° C. The reaction was then slowly quenched with ice water (4 mL) and extracted with CCl4 (3×4 mL). The organic extracts were dried over sodium sulfate and concentrated to give 4-(2-oxo-1,3-oxazolidin-3-yl)-benzenesulfonyl chloride which was used without purification. added slowly to the reaction mixture The reaction was then slowly quenched with ice water (4 mL) extracted with CCl4 (3×4 mL) The organic extracts were dried over sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2, a solution of N-(2-hydroxyethyl)aniline (500 mg, 3.65 mmol) and triethylamine (1 mL, 7.29 mmol) in THF (2 mL) was added slowly to a solution of triphosgene (360 mg, 1.21 mmol) in THF (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for one hour. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) and extracted with methylene chloride (3×4 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (5%-35% EtOAc/CH2Cl2) gave 3-phenyl-1,3-oxazolidin-2-one. LCMS (ES) m/z 164.2 (M+H)+. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) extracted with methylene chloride (3×4 mL) The organic extracts were dried over sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2, a solution of N-(2-hydroxyethyl)aniline (500 mg, 3.65 mmol) and triethylamine (1 mL, 7.29 mmol) in THF (2 mL) was added slowly to a solution of triphosgene (360 mg, 1.21 mmol) in THF (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for one hour. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) and extracted with methylene chloride (3×4 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (5%-35% EtOAc/CH2Cl2) gave 3-phenyl-1,3-oxazolidin-2-one. LCMS (ES) m/z 164.2 (M+H)+. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) extracted with methylene chloride (3×4 mL) The organic extracts were dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 43 was prepared according to the procedure described Example 2 using 2-Chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (0.1 mmol), 3-phenyl-oxazolidin-2-one and Cs2CO3 in DMF: HPLC retention time, 2.32 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected, 430.2, found, 430.2. HPLC retention time, 2.32 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2, chlorosulfonic acid (1.5 g, 12.87 mmol) was diluted in CCl4 (2 mL) and cooled to 0° C. Then 3-phenyl-1,3-oxazolidin-2-one (280 mg, 1.72 mmol) was diluted in CCl4 (2 mL) and added slowly to the reaction mixture. The reaction mixture was stirred for two hours at 0° C. The reaction was then slowly quenched with ice water (4 mL) and extracted with CCl4 (3×4 mL). The organic extracts were dried over sodium sulfate and concentrated to give 4-(2-oxo-1,3-oxazolidin-3-yl)-benzenesulfonyl chloride which was used without purification. added slowly to the reaction mixture The reaction was then slowly quenched with ice water (4 mL) extracted with CCl4 (3×4 mL) The organic extracts were dried over sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2, a solution of N-(2-hydroxyethyl)aniline (500 mg, 3.65 mmol) and triethylamine (1 mL, 7.29 mmol) in THF (2 mL) was added slowly to a solution of triphosgene (360 mg, 1.21 mmol) in THF (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for one hour. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) and extracted with methylene chloride (3×4 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (5%-35% EtOAc/CH2Cl2) gave 3-phenyl-1,3-oxazolidin-2-one. LCMS (ES) m/z 164.2 (M+H)+. The reaction was then quenched with a saturated solution of sodium bicarbonate (4 mL) extracted with methylene chloride (3×4 mL) The organic extracts were dried over sodium sulfate concentrated