89371-38-0

Basic information

• Product Name: Imidapril tert-Butyl Ester
• Synonyms: Imidapril tert-Butyl Ester
• CAS NO: 89371-38-0
• Molecular Formula: C₂₄H₃₅N₃O₆
• Molecular Weight: 461.5512
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 89371-38-0.mol

Chemical Properties

• Boiling Point: 559.349°C at 760 mmHg
• Flash Point: 292.084°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Imidapril tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: Imidapril tert-Butyl Ester(89371-38-0)
• EPA Substance Registry System: Imidapril tert-Butyl Ester(89371-38-0)

Safety Data

• Hazardous Substances Data: 89371-38-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C24H35N3O6/c1-7-32-21(29)18(14-13-17-11-9-8-10-12-17)25-16(2)20(28)27-19(15-26(6)23(27)31)22(30)33-24(3,4)5/h8-12,16,18-19,25H,7,13-15H2,1-6H3/t16-,18-,19?/m0/s1

Upstream product

• 16503-46-1 2-bromo-4-phenyl butanoic acid 
• 46460-23-5 ethyl 2-amino-4-phenyl-(2S)-butyrate 
• 83056-79-5 (4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid t-butyl ester 
• 84793-24-8 N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride 
• 83056-78-4 tert-butyl (4S)-3-(benzyloxycarbonyl)-1-methyl-2-oxoimidazolidine-4-carboxylate 
• 77999-24-7 (S)‐2‐oxoimidazolidine‐1,5‐dicarboxylate-5‐tert‐butyl ester-1‐benzyl ester 
• 82717-95-1 Benzyl (2S)-2-amino>propionate 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 82586-61-6 ethyl 2-bromo-4-phenylbutanoate 
• 943-73-7 D-homophenylalanine 
• 5440-40-4 2-(acetylamino)-4-phenylbutanoic acid 
• 1012-05-1 D,L-homophenylalanine 
• 90891-21-7 L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride 
• 195828-75-2 tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate 

Downstream Products

• 89396-94-1 Imidapril hydrochloride 
• 89371-37-9 imidapril 
• 117605-23-9 tert-Butyl (4S)-3-<(2S)-2-amino>propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate Hydrogenmaleate 

Relevant articles and documents

Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives

A strategy for the continuous flow synthesis of angiotensin converting enzyme (ACE) inhibitors is described. An optimization effort guided by in situ IR analysis resulted in a general amide coupling approach facilitated by N-carboxyanhydride (NCA) activation that was further characterized by reaction kinetics analysis in batch. The three-step continuous process was demonstrated by synthesizing 8 different ACE inhibitors in up to 88 % yield with throughputs in the range of ≈0.5 g h?1, all while avoiding both isolation of reactive intermediates and process intensive reaction conditions. The process was further developed by preparing enalapril, a World Health Organization (WHO) essential medicine, in an industrially relevant flow platform that scaled throughput to ≈1 g h?1.

Studies on angiotensin converting enzyme inhibitors. V. The diastereoselective synthesis of 2-oxoimidazolidine derivatives

A diastereoselective synthesis of imidapril (1), which is under clinical study as an antihypertensive drug based on its angiotensin converting enzyme (ACE)-inhibitory activity, was established. N-Alkylation of (2S)-2-amino-4-phenylbutyric acid ester (12) with 3-((2R)-2-methane or toluenesulfonyloxypropionyl)-2-oxoimidazolidine derivative (11) diastereoselectively proceeded in an SN2 fashion to afford tert-butyl (4S)-3-[(2S)-2-[N-[(1S)-1-ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]- 1-methyl-2-oxoimidazolidine-4-carboxylate (13), a precursor of 1. Alternatively, benzyl (2S)-2-[N-(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionate (15), which is the key building block of 13, was synthesized by the same strategy. This procedure was also applied to the synthesis of enalapril.

Process for preparing optically active 2-oxoimidazolidine derivatives

Disclosed are a process for preparing an optically active 2-oxoimidazolidine derivative of the formula: STR1 wherein R1 represents hydrogen atom or a lower alkyl group, according to the process described in the specification; and a 3-acyl-2-oxo

Studies on Angiotensin Converting Enzyme Inhibitors. 4. Synthesis and Angiotensin Converting Enzyme Inhibitory Activities of 3-Acyl-1-alkyl-2-oxoimidazolidine-4-carboxylic Acid Derivatives

(4S)-1-Alkyl-3-acyl>-2-oxoimidazolidine-4-carboxylic acid derivatives (3) were prepared by two methods.Their angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationships were discussed.The dicarboxylic acids 3a-n possessing S,S,S configuration showed potent in vitro ACE inhibitory activities with IC 50 values of 1.1x10-8-1.5x10-9 M.The most potent compound in this series, monoester 3p, had an ID 50 value of 0.24 mg/kg, po for inhibition of angiotensin I induced pressor response in normotensive rats and produced a dose-dependent decrease in systolic blood pressure of spontaneously hypertensive rats (SHRs) at doses of 1-10 mg/kg, po.