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

HRID 1935309Notes

Reaction equation

HRID 1935309 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 16.6 g (0.107 mol) of racemic 1 -(4-chloro-phenyl)-ethylamine in 41 g of methyl methoxyacetate is mixed with stirring with 1.2 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at 40° C. and the progress of the reaction is monitored by gas chromatographic sample analysis. After 2.5 hours, the conversion is 54%. At this stage, the reaction is terminated by filtering off the enzyme. In the filtrate that remains, the (S)-enantiomer of 1-(4-chloro-phenyl)-ethylamine has an ee value of 95.6%, while the (R)-enantiomer of N-(1-(4-chlorophenyl)-ethyl]-methoxyacetamide obtained has an ee value of 95.3%.

Workup

  1. stirringStirring
  2. customis continued at 40° C.
  3. customAt this stage, the reaction is terminated
  4. filtrationby filtering off the enzyme

Sources & evidence

ORD record
ord-121c6fc4117b4fa59aa2a7f32f9b976d
Source dataset
uspto-grants-2002_05
Patent number
US06387692B1

Reaction notes

Loading…