Imidaprilat

Base Information

• Chemical Name: Imidaprilat
• CAS No.: 89371-44-8
• Molecular Formula: C18H23 N3 O6
• Molecular Weight: 377.397
• UNII: WUU07Y30IA
• Nikkaji Number: J463.662G
• Wikidata: Q27888346
• NCI Thesaurus Code: C65893
• Pharos Ligand ID: SL4W81J6WFYP
• Metabolomics Workbench ID: 49616
• ChEMBL ID: CHEMBL99701
• Mol file: 89371-44-8.mol

Synonyms:3-(2-(N-(1-carboxy-3-phenylpropyl)amino)propionyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acid;6366A;imidaprilat;imidaprilat hydrochloride, (4S-(3(R*(R*)),4R*));imidaprilat hydrochloride, (4S-(3(S*(R*)),4R*))-isomer;imidaprilat, (4S-(3(R(R*)),4R*))-isomer;imidaprilat, monosodium salt, (4S-(3(R*(R*)),4R*))-isomer

Chemical Property of Imidaprilat

Chemical Property:

• Melting Point: 180-1820C
• Boiling Point: 592.1±60.0 °C(Predicted)
• PKA: 2.17±0.10(Predicted)
• PSA: 127.25000
• Density: 1.356±0.06 g/cm3(Predicted)
• LogP: 0.66440
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Acid (Slightly, Heated, Sonicated), DMSO (Slightly, Heated)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 377.15868546
• Heavy Atom Count: 27
• Complexity: 590

Purity/Quality:

96% ^*data from raw suppliers

Imidaprilat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1C(CN(C1=O)C)C(=O)O)NC(CCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C[C@@H](C(=O)N1[C@@H](CN(C1=O)C)C(=O)O)N[C@@H](CCC2=CC=CC=C2)C(=O)O
• Uses: Antihypertensive.

Technology Process of Imidaprilat

There total 19 articles about Imidaprilat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

→ (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid (89371-44-8,120294-09-9)

Guidance literature:

Reference yield: 81.0%

tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89460-20-8) → (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid (89371-44-8,120294-09-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h; under 735.5 Torr; Ambient temperature;

DOI:10.1248/cpb.40.1619

Reference yield: 79.9%

benzyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89371-43-7) → (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid (89371-44-8,120294-09-9)

Guidance literature:

palladium;

upstream raw materials:

tert-butyl (4S)-3-<(2S)-2-propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate hydrogen maleate

tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate

imidapril

2-bromo-4-phenyl butanoic acid

Refernces

• 1、 Regulska, Katarzyna,Stanisz, Beata. "Kinetics and mechanism of solid state imidapril hydrochloride degradation and its degradation impurities identification". . p. 754 - 762. Retrieved 2013/08/25.
• 2、 Kubota,Nunami,Hayashi,Hashimoto,Ogiku,Matsuoka,Ishida. "Studies on angiotensin converting enzyme inhibitors. VI. Synthesis and angiotensin converting enzyme inhibitory activities of the dicarboxylic acid derivative of imidapril and its diastereoisomers". . p. 1619 - 1622. Retrieved 2007/10/02.