Hydrochloric Acid → (S)-N-(1-phenylethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence