Methyl methoxyacetate → N-[1-(4-Chlorophenyl)ethyl]-2-methoxyacetamide

HRID 1935310Notes

Reaction equation

HRID 1935310 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][O:12][CH2:13][C:14](OC)=[O:15]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:14](=[O:15])[CH2:13][O:12][CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80507Methyl methoxyacetateHCID 978031-(4-Chlorophenyl)ethylamine

Product 1

HCID 18374039N-[1-(4-Chlorophenyl)ethyl]-2-methoxyacetamide

Procedure

At room temperature, a solution of 20.06 g (0.129 mol) of racemic 1-(4-chloro-phenyl)-ethylamine in 20 g (0.19 mol) of methyl methoxyacetate is mixed with stirring with 1 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at room temperature for one hour and the reaction is then terminated by filtering off the enzyme. The conversion is 43.9%. In the filtrate that remains, the (S)-enantiomer of 1-(4-chloro-phenyl)-ethylamine has an ee value of 61%, while the (R)-enantiomer of N-[l-(4-chlorophenyl)-ethyl]-methoxyacetamide obtained has an ee value of 98.4%.

Workup

  1. stirringStirring
  2. customthe reaction is then terminated
  3. filtrationby filtering off the enzyme

Sources & evidence

ORD record
ord-1759b7ad1fba4e21813d664cc3ac399a
Source dataset
uspto-grants-2002_05
Patent number
US06387692B1

Reaction notes

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