3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid

Base Information

• Chemical Name: 3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid
• CAS No.: 165537-73-5
• Molecular Formula: C₂₀H₂₂ClNO₄S
• Molecular Weight: 407.918
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID60432429
• Nikkaji Number: J1.758.226G
• ChEMBL ID: CHEMBL29240
• Mol file: 165537-73-5.mol

Synonyms:165537-73-5;3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid;3-[6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic Acid;SCHEMBL43629;CHEMBL29240;DTXSID60432429;HWEOXFSBSQIWSY-UHFFFAOYSA-N;BCP23809;AKOS022181167;1-NAPTHALENEPROPANOIC ACID,6-(((4-CHLOROPHENYL)SULFONYL)AMINO)-5,6,7,8-TETRAHYDRO-2-METHYL;A925104;L001513;S 18886;S-18886;S18886;3-(6-(4-Chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoic acid;3-[6-(4-chlorobenzenesulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid;3-{6-[(4-Chlorobenzene-1-sulfonyl)amino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl}propanoic acid

Chemical Property of 3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid

Chemical Property:

• Boiling Point: 591.8±60.0 °C(Predicted)
• PKA: 4.60±0.10(Predicted)
• PSA: 91.85000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 4.97310
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 407.0958071
• Heavy Atom Count: 27
• Complexity: 612

Purity/Quality:

3-(6-(4-CHLOROPHENYLSULFONAMIDO)-2-METHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-1-YL)PROPANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(CC(CC2)NS(=O)(=O)C3=CC=C(C=C3)Cl)C=C1)CCC(=O)O

Technology Process of 3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid

There total 13 articles about 3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid 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: 82.0%

methyl 3-(6-(4-chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoate (165537-95-1) → 3-(6-(4-chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoic acid (165537-73-5)

Guidance literature:

methyl 3-(6-(4-chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoate; With sodium hydroxide; In methanol; water; for 1h; Reflux; Inert atmosphere;

With hydrogenchloride; In water; ethyl acetate; Inert atmosphere;

DOI:10.1039/c4ob02302a

Reference yield:

C15H21NO2 → 3-(6-(4-chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoic acid (165537-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen / ethyl acetate / 12 h / 20 °C

2.1: sodium hydroxide / water; methanol / 1 h / Reflux; Inert atmosphere

2.2: Inert atmosphere

With hydrogen; sodium hydroxide; In methanol; water; ethyl acetate;

DOI:10.1039/c4ob02302a

Reference yield:

methyl 3-(6-hydroxy-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoate → 3-(6-(4-chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoic acid (165537-73-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -15 °C / Inert atmosphere

1.2: 12.5 h / 0 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon / ethyl acetate

3.1: hydrogen / ethyl acetate / 12 h / 20 °C

4.1: sodium hydroxide / water; methanol / 1 h / Reflux; Inert atmosphere

4.2: Inert atmosphere

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; 1.1: |Mitsunobu Displacement;

DOI:10.1039/c4ob02302a

upstream raw materials:

methyl 3-(6-(4-chlorophenylsulfonamido)-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)propanoate

6-(4-Chlorophenylsulfonyl)amino-2-oxo-5,6,7,8-tetrahydro-2H-benzo[e]pyran

6-(4-Chlorophenylsulfonyl)amino-2-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxaldehyde

(E)-3-[6-(4-Chloro-benzenesulfonylamino)-2-methyl-5,6,7,8-tetrahydro-naphthalen-1-yl]-acrylic acid methyl ester

Refernces

• 1、 Cimetiere, Bernard,Dubuffet, Thierry,Muller, Olivier,Descombes, Jean-Jacques,Simonet, Serge,Laubie, Michel,Verbeuren, Tony J.,Lavielle, Gilbert. "Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists". . p. 1375 - 1380. Retrieved 2007/10/03.