N-[(1S)-1-phenylethyl]acetamide

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 1 g (6.13 mmol) racemic N-acetyl 1-phenylethylamine (+/−)-1a, partially dissolved in 100 ml 0.1 M phosphate buffer pH 7.0, 100 ml (25.3 units) acylase from Arthrobacter aurescens Ac5R is added and the mixture is shaken (100 rpm) at 20° C. for 27 hours. After acidification (pH 2) by addition of HCl the reaction mixture is extracted three times with 100 ml dichloromethane. The combined organic layers are dried (MgSO4) and the solvent is distilled off after filtration, yielding 0.496 g (49.6%) of (S)-N-acetyl 1-phenylethylamine (−)-1a ([α]D20=−138.0° (c=1.0 EtOH), enantiomeric ratio S/R=96.8:3.2) as a white solid. The aqueous phase is neutralized by addition of NaHCO3 and extracted again with dichloromethane. Usual workup leads to 0.323 g (43.5%) of (R)-1-phenylethylamine (+)-1b ([α]D20=+29.4° (c=2.2 EtOH), enantiomeric ratio R/S=99.7:0.3) as colorless oil. is added is extracted three times with 100 ml dichloromethane The combined organic layers are dried (MgSO4) the solvent is distilled off after filtration

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of (S)-(−)-1-phenylethylamine (121 g) and triethylamine (168 ml) in dichloroethane (1200 ml) was added dropwise acetyl chloride (78.2 ml) over 1 hr under ice-cooling and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water (1000 ml) and the organic layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (143.4 g) as pale-yellow crystals, m.p.=99-101° C. cooling the organic layer was separated The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated