138279-20-6

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-
• CAS NO: 138279-20-6
• Molecular Formula: C21H24N2O8
• Molecular Weight: 432.43
• Mol File: 138279-20-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-(138279-20-6)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-(138279-20-6)

Safety Data

• Hazardous Substances Data: 138279-20-6(Hazardous Substances Data)

Upstream product

• 74936-81-5 1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid 
• 18997-19-8 Chloromethyl pivalate 
• 138279-16-0 bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 138299-10-2 bis(pivaloyloxymethyl) 1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 123973-70-6 1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 

Downstream Products

• 138279-12-6 (S)-(+)-methyl pivaloyloxymethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 122417-22-5 (R)-2-cyano-1,4-dihydro-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-5-pyridinecarboxylate 
• 158612-42-1 (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 158612-43-2 (R)-methyl pivaloyloxymethyl 2-bromomethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 158612-41-0 (R)-methyl pivaloyloxymethyl 2-formyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 109545-30-4 (+)-Nilvadipine 
• 170308-21-1 (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 
• 111495-28-4 (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 
• 178484-40-7 (R)-5-Bromo-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl 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.

Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines

Two enantiomers of 1,4-dihydropyridine compounds have been obtained with high enantiomeric purity by lipase-catalyzed hydrolysis in organic solvent saturated with water. Enantioselectivity of this reaction is dependent on the solvent used.