3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, 1,1-dimethylethyl ester, (3S)-

Base Information

• Chemical Name: 3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, 1,1-dimethylethyl ester, (3S)-
• CAS No.: 82586-56-9
• Molecular Formula: C₂₉H₃₈N₂O₅
• Molecular Weight: 494.631
• DSSTox Substance ID: DTXSID901100058
• Mol file: 82586-56-9.mol

Synonyms:SCHEMBL5967534;DTXSID901100058;3-ISOQUINOLINECARBOXYLIC ACID, 2-[(2S)-2-[[(1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]-1-OXOPROPYL]-1,2,3,4-TETRAHYDRO-, 1,1-DIMETHYLETHYL ESTER, (3S)-;82586-56-9

Chemical Property of 3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, 1,1-dimethylethyl ester, (3S)-

Chemical Property:

• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 494.27807232
• Heavy Atom Count: 36
• Complexity: 742

Purity/Quality:

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)N2CC3=CC=CC=C3CC2C(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC=CC=C3C[C@H]2C(=O)OC(C)(C)C

Technology Process of 3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, 1,1-dimethylethyl ester, (3S)-

There total 4 articles about 3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, 1,1-dimethylethyl ester, (3S)- 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: 78.0%

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester (77497-74-6,189094-06-2,82716-91-4) + N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride (80828-26-8) → tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (82586-56-9)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm00160a026

Reference yield:

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride (84793-24-8) + (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester (77497-74-6,189094-06-2,82716-91-4) → tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (82586-56-9)

Guidance literature:

acetic acid; In toluene; at 15 - 35 ℃; for 0.583333h;

Reference yield:

L-Tic-OH (74163-81-8) → tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (82586-56-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄ / dioxane / 17 h / Ambient temperature

2: 78 percent / Et₃N, DCC, 1-hydroxybenzotriazole / tetrahydrofuran / Ambient temperature

With sulfuric acid; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm00160a026

upstream raw materials:

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

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

L-Tic-OH

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

Downstream raw materials:

quinapril hydrochloride

isobutene

(S)-2-{(S)-2-[((S)-1-Ethoxycarbonyl-3-phenyl-propyl)-methyl-amino]-propionyl}-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

<3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid, ethyl ester

Refernces

• 1、 -. "PREPARATION OF QUINAPRIL HYDROCHLORIDE". Page column 5. . Retrieved 2008/06/13.