67617-67-8

Upstream product

• 67617-64-5 N-(2,6-dimethylphenyl)alanine 
• 107-18-6 allyl alcohol 
• 52888-49-0 methyl N-(2,6-dimethylphenyl)alaninate 
• 67617-63-4 (S)-methyl 2-(2,6-dimethylphenylamino)propanoate 

Downstream Products

• 57646-32-9 (2R)-2-[(2,6-dimethylphenyl)amino]propanoic acid 
• 57646-33-0 methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate 
• 57837-19-1 methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate 
• 67617-68-9 N-chloroacetyl-N-(2,6-dimethylphenyl)-alanine allyl ester 

Relevant academic research and scientific papers

Enzyme-catalyzed preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate: A key intermediate for (R)-metalaxyl

A biocatalytic approach for the production of (R)-metalaxyl, mefenoxam, has been developed. A practical synthesis of methyl (R)-N-(2,6-dimethylphenyl) alaninate, a key intermediate for (R)-metalaxyl, has been developed by the use of lipase-catalyzed hydrolytic kinetic resolution and chemical racemization of the remaining ester. At high concentrations in aqueous media (300 g/L) lipases were stable and gave moderate to good conversions and excellent enantioselectivities (>98% ee). A simple extraction procedure was used to separate the acid product from the remaining ester and the acid was esterified with methanol to give methyl (R)-N-(2,6-dimethylphenyl)alaninate without any reduction in enantiomeric excess (>98% ee). Subsequent chemical coupling with methoxyacetyl chloride provided enantiomerically pure (R)-metalaxyl (>98% ee) without racemization.

Combating fungi with N-chloroacetyl-N-(2,6-di-substituted phenyl)-alanine esters

N-Chloroacetyl-N-(2,6-di-substituted phenyl)-alanine esters of the formula STR1 in which R represents alkyl with 3 or more carbon atoms, alkenyl, alkynyl, halogenoalkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsul