Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)-

Base Information

• Chemical Name: Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)-
• CAS No.: 920289-29-8
• Molecular Formula: C₂₈H₂₉FN₂O₄
• Molecular Weight: 476.548
• UNII: WO23I2827Q
• ChEMBL ID: CHEMBL4859268
• Metabolomics Workbench ID: 155506
• Wikidata: Q76507120
• Mol file: 920289-29-8.mol

Synonyms:AGG-523;920289-29-8;UNII-WO23I2827Q;WAY-266523;WO23I2827Q;PF-5212371;PF-05212371;Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)-;CHEMBL4859268;(4S)-5-[[1-(4-fluorophenyl)-2-methylpropan-2-yl]amino]-5-oxo-4-[(4-phenylbenzoyl)amino]pentanoic acid;4-(S)-(((Biphenyl-4-yl)carbonyl)amino)-4-((2-(4-fluorophenyl)-1,1-dimethylethyl)carbamoyl)butyric acid;SCHEMBL2245079;JWQMTWCFNZSLNR-DEOSSOPVSA-N;GLXC-26407;BDBM50575719;DB15460;BA178432;AGG-523, AGG 523, AGG523, PF-05212371, WAY-266523;(S)-4-([1,1'-biphenyl]-4-carboxamido)-5-((1-(4-fluorophenyl)-2-methylpropan-2-yl)amino)-5-oxopentanoic acid;4(S)-[(Biphenyl-4-carbonyl)-amino]-4-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylcarbamoyl]-butyric acid

Chemical Property of Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)-

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 476.21113557
• Heavy Atom Count: 35
• Complexity: 706

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(CC1=CC=C(C=C1)F)NC(=O)C(CCC(=O)O)NC(=O)C2=CC=C(C=C2)C3=CC=CC=C3
• Isomeric SMILES: CC(C)(CC1=CC=C(C=C1)F)NC(=O)[C@H](CCC(=O)O)NC(=O)C2=CC=C(C=C2)C3=CC=CC=C3
• Recent ClinicalTrials: Study Evaluating AGG-523 in Subjects With Severe Osteoarthritis Requiring Total Knee Replacement

Technology Process of Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)-

There total 5 articles about Pentanoic acid, 4-(((1,1'-biphenyl)-4-ylcarbonyl)amino)-5-((2-(4-fluorophenyl)-1,1-dimethylethyl)amino)-5-oxo-, (4S)- 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: 92.0%

4(S)-[(Biphenyl-4-carbonyl)-amino]-4-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylcarbamoyl]-butyric acid tert-butyl ester → 4(S)-[(Biphenyl-4-carbonyl)-amino]-4-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylcarbamoyl]-butyric acid (920289-29-8)

Guidance literature:

4(S)-[(Biphenyl-4-carbonyl)-amino]-4-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylcarbamoyl]-butyric acid tert-butyl ester; With trifluoroacetic acid; In toluene; at 5 - 20 ℃; for 4 - 6h;

With potassium acetate; In water; ethyl acetate;

Reference yield:

N2-(1,1'-biphenyl-4-ylcarbonyl)-N1-[2-(4-fluorophenyl)-1,1-dimethylethyl]-L-α-glutamine monohydrate → 4(S)-[(Biphenyl-4-carbonyl)-amino]-4-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylcarbamoyl]-butyric acid (920289-29-8)

Guidance literature:

at 83 - 110 ℃; for 23h; Product distribution / selectivity;

Reference yield:

tert-butyl N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N1-[2-(4-fluorophenyl)-1,1-dimethylethyl]-L-α-glutaminate (920289-26-5) → 4(S)-[(Biphenyl-4-carbonyl)-amino]-4-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylcarbamoyl]-butyric acid (920289-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride; water / heptane(s)

2: triethylamine / tetrahydrofuran; tert-butyl methyl ether

3: trifluoroacetic acid / toluene / Heating

With hydrogenchloride; water; triethylamine; trifluoroacetic acid; In tetrahydrofuran; tert-butyl methyl ether; heptane(s); toluene;

upstream raw materials:

tert-butyl N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N1-[2-(4-fluorophenyl)-1,1-dimethylethyl]-L-α-glutaminate

2-(4-fluoro-phenyl)-1,1-dimethyl-ethylamine hydrochloride

Downstream raw materials:

N-(1,1'-biphenyl-4-ylcarbonyl)-L-glutamic acid

1-(4-fluorophenyl)-2-methylpropan-2-amine

biphenyl-4-carboxylic acid

Refernces

• 1、 -. "Glutamate aggrecanase inhibitors". Page/Page column 41; 51. . Retrieved 2008/06/13.
• 2、 -. "METHODS FOR PREPARING GLUTAMIC ACID DERIVATIVES AND INTERMEDIATES THEREOF". Page/Page column 50. . Retrieved 2008/06/13.