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

HRID 1977567Notes

Reaction equation

HRID 1977567 reaction equation
[C:1]([NH:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2].Cl>P([O-])([O-])([O-])=O>[C:1]([NH:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 222023N-(1-phenylethyl)acetamide

Product 1

HCID 737096(S)-N-(1-phenylethyl)acetamideYield 49.6%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  1. additionis added
  2. extractionis extracted three times with 100 ml dichloromethane
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. distillationthe solvent is distilled off
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-56cdf6b8eb144de2890279855501518b
Source dataset
uspto-grants-2001_05
Patent number
US06235516B1

Reaction notes

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