(2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-(4-phenylphenyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: (2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-(4-phenylphenyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• CAS No.: 169545-27-1
• Molecular Formula: C₃₆H₃₅N₃O₄
• Molecular Weight: 573.692
• DSSTox Substance ID: DTXSID20415511
• Nikkaji Number: J2.386.715J
• Wikidata: Q27078113
• Pharos Ligand ID: BPPMCL4MA835
• ChEMBL ID: CHEMBL72410
• Mol file: 169545-27-1.mol

Synonyms:IRL 2500;IRL-2500;N-(3,5-dimethylbenzoyl)-N-methyl-(4-phenylphenyl)alanyl-tryptophan

Chemical Property of (2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-(4-phenylphenyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoic acid

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 2.56E-34mmHg at 25°C
• Melting Point: 83-88oC
• Refractive Index: 1.652
• Boiling Point: 893.7 °C at 760 mmHg
• Flash Point: 494.3 °C
• PSA: 102.50000
• Density: 1.246g/cm³
• LogP: 6.33800
• Storage Temp.: Desiccate at RT
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 573.26275661
• Heavy Atom Count: 43
• Complexity: 933

Purity/Quality:

99% ^*data from raw suppliers

IRL-2500 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)C(=O)N(C)C(CC2=CC=C(C=C2)C3=CC=CC=C3)C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)O)C
• Isomeric SMILES: CC1=CC(=CC(=C1)C(=O)N(C)[C@H](CC2=CC=C(C=C2)C3=CC=CC=C3)C(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)O)C
• Uses: IRL 2500 is a potent endothelin ETB selective antagonist.

Technology Process of (2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-(4-phenylphenyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoic acid

There total 13 articles about (2S)-2-[[(2R)-2-[(3,5-dimethylbenzoyl)-methylamino]-3-(4-phenylphenyl)propanoyl]amino]-3-(1H-indol-3-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:

(S)-methyl 2-((R)-3-([1,1‘-biphenyl]-4-yl)-2-(N,3,5-trimethylbenzamido)propanamido)-3-(1H-indol-3-yl)propanoate → IRL 2500 (169545-27-1)

Guidance literature:

With water; lithium hydroxide; In methanol; at 20 ℃; for 6h;

Reference yield:

N-methyl-(D)-(4-phenylphenyl)alanine methyl ester (173189-77-0) → IRL 2500 (169545-27-1)

Guidance literature:

Multi-step reaction with 3 steps

2: aq. LiOH / methanol

With lithium hydroxide; In methanol;

DOI:10.1016/0960-894X(96)00421-0

Reference yield:

3,5-dimethylbenzoyl chloride (6613-44-1) → IRL 2500 (169545-27-1)

Guidance literature:

Multi-step reaction with 3 steps

2: aq. LiOH / methanol

With lithium hydroxide; In methanol;

DOI:10.1016/0960-894X(96)00421-0

upstream raw materials:

(S)-tryptophan methyl ester hydrochloride

(R)-3-Biphenyl-4-yl-2-[(3,5-dimethyl-benzoyl)-methyl-amino]-propionic acid

3,5-dimethylbenzoyl chloride

N-methyl-(D)-(4-phenylphenyl)alanine methyl ester

Refernces

• 1、 -. "Antagonists of endothelin receptors". . . Retrieved 2008/06/13.