100427-51-8

Basic information

• Product Name: Butanoic acid, 3-oxo-,2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl ester
• Synonyms: Butanoic acid, 3-oxo-,2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl ester;3-Oxo-butanoic acid 2-[(3,3-diphenylpropyl)methylamino]-1,1-dimethylethyl ester;1-((3,3-diphenylpropyl)(Methyl)aMino)-2-Methylpropan-2-yl 3-oxobutanoate
• CAS NO: 100427-51-8
• Molecular Formula: C₂₄H₃₁NO₃
• Molecular Weight: 381.50784
• Mol File: 100427-51-8.mol

Chemical Properties

• Appearance: /
• Density: 1.062±0.06 g/cm3 (20 ºC 760 Torr)
• Solubility: Chloroform, DCM, DMSO
• CAS DataBase Reference: Butanoic acid, 3-oxo-,2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-oxo-,2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl ester(100427-51-8)
• EPA Substance Registry System: Butanoic acid, 3-oxo-,2-[(3,3-diphenylpropyl)MethylaMino]-1,1-diMethylethyl ester(100427-51-8)

Safety Data

• Hazardous Substances Data: 100427-51-8(Hazardous Substances Data)

Usage

Uses

3-Oxo-butanoic Acid 2-[(3,3-Diphenylpropyl)methylamino]-1,1-dimethylethyl Ester is an intermediate in synthesizing 5-Ethyl-demethyl Lercanidipine (E913200), which is an impurity of Lercanidipine (L179000), a dihydropyridine calcium channel blocker.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 100442-33-9 2,N-dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol 
• 28075-29-8 N-methyl-3,3-diphenylpropylamine 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 929212-20-4 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid 2-[(3,3-diphenylpropyl)methylamino]-1,1-dimethyl ethyl ester hydrochloride 
• 132866-11-6 lercanidipine hydrochloride 
• 786625-22-7 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl} ester 5-ethyl ester 
• 100427-26-7 lercanidipine 
• 210579-45-6 2-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl ester 

Relevant articles and documents

LERCANIDIPINE HYDROCHLORIDE POLYMORPHS AND AN IMPROVED PROCESS FOR PREPARATION OF 1,1,N-TRIMETHYL-N-(3,3-DIPHENYLPROPYL)-2-AMINOETHYL ACETOACETATE

Disclosed herein is an improved, commercially viable and industrially advantageous process for the preparation of substantially pure Lercanidipine intermediate, 1,1,N- trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl acetoacetate. The intermediate is useful for preparing Lercanidipine, or a pharmaceutically acceptable salt thereof, in high yield and purity. The present invention further provides a novel crystalline form of Lercanidipine hydrochloride and a process for its preparation. The present invention also provides a process for the preparation of amorphous form of Lercanidipine hydrochloride.

Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6- dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenylpropylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4- dihydropyridines binding site labelled by 3H-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375- lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries.