400884-08-4

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-, methyl (2-methyl-1-oxopropoxy)methyl ester
• CAS NO: 400884-08-4
• Molecular Formula: C22H25F2NO7
• Molecular Weight: 453.44
• Mol File: 400884-08-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-, methyl (2-methyl-1-oxopropoxy)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-, methyl (2-methyl-1-oxopropoxy)methyl ester(400884-08-4)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-, methyl (2-methyl-1-oxopropoxy)methyl ester(400884-08-4)

Safety Data

• Hazardous Substances Data: 400884-08-4(Hazardous Substances Data)

Upstream product

• 71653-64-0 o-difluoromethoxybenzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 61644-18-6 chloromethyl isobutyrate 
• 103124-12-5 4-[2-(difluoromethoxy)phenyl]-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydro-3-pyridinecarboxylic acid 
• 400884-04-0 3-(2-cyanoethyl) 5-methyl 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate 
• 400884-01-7 2-[2-(difluoromethoxy)benzylidene]methyl acetoacetate 

Downstream Products

• 400884-19-7 (-)-(4S)-4-[2-(difluoromethoxy)phenyl]-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydro-3-pyridinecarboxylic acid 
• 442682-41-9 (-)-3-[(isobutyryloxy)methyl] 5-methyl (4R)-4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate 

Relevant articles and documents

Effect of acyl chain length and branching on the enantioselectivity of Candida rugosa lipase in the kinetic resolution of 4-(2-difluoromethoxyphenyl)-substituted 1,4-dihydropyridine 3,5-diesters

Since 2,6-dimethyl-4-aryl-1,4-dihydropyridine 3,5-diesters themselves are not hydrolyzed by commercially available hydrolases, derivatives with spacers containing a hydrolyzable group were prepared. Seven acyloxymethyl esters of 5-methyl- and 5-(2-propoxyethyl) 4-[2-(difluoromethoxy)-pheny]l-2,6-dimethyl-1,4-dihydro-3, 5-pyridinedicarboxylate were synthesized and subjected to Candida rugosa lipase (CRL) catalyzed hydrolysis in wet diisopropyl ether. A methyl ester at the 5-position and a long or branched acyl chain at C3 gave the highest enantiomeric ratio (E values). The most stereoselective reaction (E = 21) was obtained with 3- [(isobutyryloxy)methyl] 5-methyl 4-(2-difluoromethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3, 5-dicarboxylate, and this compound was used to prepare both enantiomers of 3-methyl 5-(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3, 5-pyridinedicarboxylate. The absolute configuration of the enzymatically produced carboxylic acid was established to be 4R by X-ray crystallographic analysis of its 1-(R)-phenylethyl amide.