138693-53-5

Upstream product

• 123973-70-6 1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 
• 138279-15-9 bis(propionyloxymethyl) 1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 

Downstream Products

• 138299-13-5 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-propionyloxymethyl ester 
• 138299-12-4 1-Methoxymethyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-propionyloxymethyl ester 

Relevant academic research and scientific papers

Lipase-catalyzed enantioselective hydrolysis of bis(acyloxymethyl) 1,4- dihydro-3,5-pyridinedicarboxylates leading to optically active medicines

Chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates and 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase catalyzed hydrolysis of bis(acyloxymethyl) 1,4-dihydro- 3,5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.

Acyloxymethyl as an activating group in lipase-catalyzed enantioselective hydrolysis. A versatile approach to chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates

The first practical syntheses of chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates, which are attractive compounds as new calcium antagonists, were realized by lipase-catalyzed enantioselective hydrolysis of the acyloxymethyl esters. The monoesters obtained were revealed to have high optical purity and demonstrated to be useful chiral synthons.