Indolapril

Base Information

• Chemical Name: Indolapril
• CAS No.: 80876-01-3
• Molecular Formula: C₂₄H₃₄N₂O₅
• Molecular Weight: 430.544
• UNII: R07Y89H0HB
• DSSTox Substance ID: DTXSID701033605
• Nikkaji Number: J33.885K
• Wikidata: Q27287605
• NCI Thesaurus Code: C174904
• ChEMBL ID: CHEMBL331369
• Mol file: 80876-01-3.mol

Synonyms:1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)alanyl)octahydro-1H-indole-2-carboxylic acid;CI 907;CI-907;Indolapril;Indolapril hydrochloride;PD 109,763-2;PD-109,763-2;Sch 31846;Sch-31846

Chemical Property of Indolapril

Chemical Property:

• Vapor Pressure: 1.55E-16mmHg at 25°C
• Boiling Point: 626°C at 760 mmHg
• Flash Point: 332.4°C
• PSA: 95.94000
• Density: 1.181g/cm³
• LogP: 3.10210
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 430.24677219
• Heavy Atom Count: 31
• Complexity: 634

Purity/Quality:

98%Min ^*data from raw suppliers

INDOLAPRIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C3CCCCC3CC2C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@H]3CCCC[C@H]3C[C@H]2C(=O)O
• Uses: Antihypertensive.

Technology Process of Indolapril

There total 45 articles about Indolapril 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: 97.0%

tert-butyl (2S,3aR,7aS)-1-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)octahydro-1H-indole-2-carboxylate → trandolapril (87679-37-6,80876-01-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0037-1612306

Reference yield:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester (82717-90-6) + [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) → trandolapril (87679-37-6,80876-01-3)

Guidance literature:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester; [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 20 - 25 ℃; for 3h;

With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; at 25 - 35 ℃; under 1471.14 - 2206.72 Torr;

With diethyl ether; for 0.0833333 - 0.166667h;

Reference yield:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester (82717-90-6) + [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) → N-[1-(S)-carbethoxy-3-phenylpropyl]-(S)-alanyl-2R,3aS,7aR-octahydroindole-2-carboxylic acid (852921-57-4,80876-01-3) + trandolapril (87679-37-6,80876-01-3)

Guidance literature:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester; [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 20 - 25 ℃; for 3h;

With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; at 25 - 35 ℃; under 1471.14 - 2206.72 Torr;

upstream raw materials:

(2R,3aR,7aR)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester

2-carbethoxyindole

(+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid

(2S,3aS,7aS)-Octahydro-indole-2-carboxylic acid ethyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE". Page/Page column 23. . Retrieved 2015/01/07.
• 2、 -. "Method for producing {n-[1-(s)-carbalkoxy-3-phenylpropyl]-s-alanyl-2s, 3ar, 7as-octahydroindole-2-carboxylic acid} compounds". . . Retrieved 2008/06/13.