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

HRID 1935307Notes

Reaction equation

HRID 1935307 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]>C(OC)(C)(C)C>[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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

At room temperature, a solution of 7.8 g (0.05 mol) of racemic 1-(4-chloro-phenyl)-ethylamine in 35 ml of methyl tert-butyl ether is mixed with stirring with 8.32 g (0.08 mol) of methyl methoxyacetate and then with 0.39 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at room temperature and the progress of the reaction is monitored by gas chromatographic sample analysis. After 4.5 hours, the conversion is 55%. 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 98.1%, while the (R)-enantiomer of N-(1-(4-chlorophenyl)-ethyl]-methoxyacetamide obtained has an ee value of 96%.

Workup

  1. customis continued at room temperature
  2. customAt this stage, the reaction is terminated
  3. filtrationby filtering off the enzyme

Sources & evidence

ORD record
ord-c7c2f0d03e6b4bd9ba2255448a1763c7
Source dataset
uspto-grants-2002_05
Patent number
US06387692B1

Reaction notes

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