N,N-diethyl-2-hydroxy-2-phenylacetamide

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

Procedure: To a solution of N,N-diethyl-2-hydroxy-2-phenyl-acetamide (0.18 g, 0.9 mmol), Et3N (0.36 mL, 2.6 mmol), and CH2Cl2 (10 mL) at 0° C. was added methane sulfonyl chloride (0.08 mL, 1.0 mmol). After stirring for an hour, the reaction mixture was quenched with H2O (5 mL) and extracted with CH2Cl2 (3×25 mL). The orgranic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure. Chromatography of the resulting residue (Si02: EtOAc:Hex) yielded the title compound. the reaction mixture was quenched with H2O (5 mL) extracted with CH2Cl2 (3×25 mL) dried (Na2SO4) the solvent was evaporated under reduced pressure

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

Procedure: 2-Hydroxy-2-phenylacetic acid (500 mg, 3.29 mmol) was dissolved in dichloromethane (7.5 mL). To this, pyridine (0.532 mL, 6.58 mmol), DMAP (40 mg, 0.33 mmol) and trimethylsilyl chloride (0.835 mL, 6.58 mmol) were added at room temperature and the mixture was stirred for 7.8 hours. After the reaction mixture was cooled to 0° C., N,N-dimethylformamide (0.050 mL) and oxalyl chloride (0.301 mL, 3.45 mmol) were added thereto, and the mixture was stirred at a temperature of 0° C. to room temperature for 1 hour. After the reaction mixture was cooled to 0° C. again, a pyridine solution (0.878 mL) of diethylamine (0.374 mL, 3.62 mmol) was added thereto, and the mixture was stirred at a temperature of 0° C. to room temperature for 2 hours. Then, a methanol solution (5 mL) of citric acid (695 mg, 3.62 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 12 hours. After addition of ethyl acetate, the reaction mixture was filtered. One mol/L hydrochloric acid was added to the filtrate, and extraction with ethyl acetate was performed, followed by washing with saturated sodium carbonate and brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and thereby N,N-diethyl-2-hydroxy-2-phenylacetamide (Compound ED) (606 mg, yield: 89%) was obtained. the mixture was stirred at a temperature of 0° C. to room temperature for 1 hour After the reaction mixture was cooled to 0° C. again the mixture was stirred at a temperature of 0° C. to room temperature for 2 hours the mixture was stirred at room temperature for 12 hours the reaction mixture was filtered One mol/L hydrochloric acid was added to the filtrate, and extraction with ethyl acetate by washing with saturated sodium carbonate and brine drying over anhydrous sodium sulfate The solvent was evaporated off under reduced pressure