88977-32-6

Basic information

• Product Name: (E)-2-Cyanoethyl 3-AMinobut-2-enoate
• Synonyms: (E)-2-Cyanoethyl 3-AMinobut-2-enoate;2-cyanoethyl (E)-3-aminobut-2-enoate
• CAS NO: 88977-32-6
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.1665
• Mol File: 88977-32-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-2-Cyanoethyl 3-AMinobut-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-Cyanoethyl 3-AMinobut-2-enoate(88977-32-6)
• EPA Substance Registry System: (E)-2-Cyanoethyl 3-AMinobut-2-enoate(88977-32-6)

Safety Data

• Hazardous Substances Data: 88977-32-6(Hazardous Substances Data)

Usage

Description

(E)-2-Cyanoethyl 3-Aminobut-2-enoate is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by its cyanoethyl and aminobutenoate functional groups, which contribute to its reactivity and potential applications in chemical reactions and drug development.

Uses

Used in Pharmaceutical Industry:
(E)-2-Cyanoethyl 3-Aminobut-2-enoate is used as a synthetic intermediate for the production of Felodipine-d3 (F232377), a labelled dihydropyridine calcium channel blocker. (E)-2-Cyanoethyl 3-AMinobut-2-enoate plays a crucial role in the development of pharmaceuticals that target the cardiovascular system, specifically for the treatment of hypertension and angina.
Additionally, due to its unique chemical structure, (E)-2-Cyanoethyl 3-Aminobut-2-enoate may also be utilized in the synthesis of other active pharmaceutical ingredients, potentially expanding its applications in the pharmaceutical industry. Its versatility as a synthetic intermediate makes it a valuable compound for researchers and chemists working in drug development and medicinal chemistry.

Upstream product

• 65193-87-5 2-cyanoethylacetoacetate 

Downstream Products

• 210829-70-2 4-Benzo[1,3]dioxol-5-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-benzyl ester 5-(2-cyano-ethyl) ester 
• 219553-54-5 3-(2-cyanoethoxycarbonyl)-5-(N-methylcarboxamido)-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine 
• 261728-70-5 bis(2-cyanoethyl) 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate 
• 864969-65-3 3-(2-cyanoethyl) 4-[2-(difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate 
• 400884-04-0 3-(2-cyanoethyl) 5-methyl 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate 
• 261728-63-6 bis(2-cyanoethyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 175688-78-5 4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-ethyl ester 
• 142161-47-5 4-(2-chlorophenyl)-5-<(2-cyanoethoxy)carbonyl>-1,4-dihydro-3-(ethoxycarbonyl)-6-methyl-2-<4-(2-methylimidazo<4,5-c>pyrid-1-yl)phenyl>pyridine 
• 74936-70-2 3-(2-cyanoethyl) 5-isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-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.