2-{2-[(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}isoquinolin-2-ium

Base Information

• Chemical Name: 2-{2-[(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}isoquinolin-2-ium
• CAS No.: 82586-54-7
• Molecular Formula: C32H36N2O5.C4H4O4
• Molecular Weight: 528.648
• DSSTox Substance ID: DTXSID40700613
• Mol file: 82586-54-7.mol

Synonyms:DTXSID40700613;A840380;2-[[1-(2-isoquinolin-2-iumyl)-1-oxopropan-2-yl]amino]-4-phenylbutanoic acid ethyl ester;2-{2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}isoquinolin-2-ium;ethyl 2-[(1-isoquinolin-2-ium-2-yl-1-oxidanylidene-propan-2-yl)amino]-4-phenyl-butanoate

Chemical Property of 2-{2-[(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}isoquinolin-2-ium

Chemical Property:

• Melting Point: 139 ºC
• PSA: 84.94000
• LogP: 4.55470
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 391.20216773
• Heavy Atom Count: 29
• Complexity: 532

Purity/Quality:

99% ^*data from raw suppliers

QUINAPRIL BENZYLESTER 98.00% ^*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)[N+]2=CC3=CC=CC=C3C=C2
• Uses: Quinapril Benzyl Ester is used in preparation of Quinapril Hydrochloride.

Technology Process of 2-{2-[(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}isoquinolin-2-ium

There total 10 articles about 2-{2-[(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}isoquinolin-2-ium 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: 0.69%

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2) + N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride (80828-26-8) + N,N-diethylchloromethyleneiminium chloride → quinapril benzyl ester (82586-54-7)

Guidance literature:

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride; N,N-diethylchloromethyleneiminium chloride; In dichloromethane; at 20 ℃; for 0.13h; Flow reactor;

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester; In dichloromethane; at 20 ℃; for 0.0216667h; Flow reactor;

In aq. phosphate buffer; at 20 ℃; for 0.0283333h; pH=10; pH-value; Flow reactor;

DOI:10.1002/chem.201904400

Reference yield:

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2) + N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester (124492-03-1) → 2-Mercaptobenzothiazole (149-30-4,118090-09-8) + quinapril benzyl ester (82586-54-7)

Guidance literature:

With triethylamine; In dichloromethane; at -15 - -10 ℃; for 4h;

DOI:10.1081/SCC-200048435

Reference yield:

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride (80828-26-8) → quinapril benzyl ester (82586-54-7)

Guidance literature:

benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt; With triethylamine; In dichloromethane; at 0 - 5 ℃; for 0.166667h;

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride; In dichloromethane; at -20 - 25 ℃; for 1h;

upstream raw materials:

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester

N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride

N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

Downstream raw materials:

quinapril

quinapril hydrochloride

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE". Page/Page column 21; 22. . Retrieved 2015/01/07.
• 2、 -. "CRYSTALLINE FORM OF QUINAPRIL HYDROCHLORIDE AND PROCESS FOR PREPARING THE SAME". Page 25;13;16. . Retrieved 2008/06/13.