138279-19-3

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-
• CAS NO: 138279-19-3
• Molecular Formula: C23H27Cl2NO7
• Molecular Weight: 500.376
• Mol File: 138279-19-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-(138279-19-3)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-(138279-19-3)

Safety Data

• Hazardous Substances Data: 138279-19-3(Hazardous Substances Data)

Upstream product

• 141600-77-3 4-(2,3-Dichloro-phenyl)-1-methoxymethyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 
• 18997-19-8 Chloromethyl pivalate 
• 138299-11-3 bis(pivaloyloxymethyl) 4-(2,3-dichlorophenyl)-1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 

Downstream Products

• 141600-78-4 (S)-(+)-methyl pivaloyloxymethyl 4-(2,3-dichlorophenyl)-1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 138279-28-4 (+)-methyl pivaloyloxymethyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 105580-45-8 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester 
• 141600-80-8 (S)-(+)-methyl pivaloyloxymethyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 105580-46-9 (R)-(+)-4-(2,3-dichlorophenyl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylic acid 
• 138279-25-1 4-(2,3-Dichloro-phenyl)-1-methoxymethyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2,2-dimethyl-propionyloxymethyl) ester 5-methyl ester 

Relevant articles and documents

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.