(S)-4-fluoro-4-Methyl-2-((S)-2,2,2-trifluoro-1-(4'-(Methylsulfonyl)biphenyl-4-yl)ethylaMino)pentanoic acid

Base Information

• Chemical Name: (S)-4-fluoro-4-Methyl-2-((S)-2,2,2-trifluoro-1-(4'-(Methylsulfonyl)biphenyl-4-yl)ethylaMino)pentanoic acid
• CAS No.: 875272-89-2
• Molecular Formula: C21H23F4NO4S
• Molecular Weight: 461.478
• Mol file: 875272-89-2.mol

Synonyms:(S)-4-fluoro-4-Methyl-2-((S)-2,2,2-trifluoro-1-(4'-(Methylsulfonyl)biphenyl-4-yl)ethylaMino)pentanoic acid

Chemical Property of (S)-4-fluoro-4-Methyl-2-((S)-2,2,2-trifluoro-1-(4'-(Methylsulfonyl)biphenyl-4-yl)ethylaMino)pentanoic acid

Chemical Property:

• PSA: 91.85000
• LogP: 6.01320

Purity/Quality:

99%+, ^*data from raw suppliers

(S)-4-fluoro-4-methyl-2-((S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)biphenyl-4-yl)ethylamino)pentanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-4-fluoro-4-Methyl-2-((S)-2,2,2-trifluoro-1-(4'-(Methylsulfonyl)biphenyl-4-yl)ethylaMino)pentanoic acid

There total 12 articles about (S)-4-fluoro-4-Methyl-2-((S)-2,2,2-trifluoro-1-(4'-(Methylsulfonyl)biphenyl-4-yl)ethylaMino)pentanoic 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: 86.2%

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone (893407-18-6) + sodium cyanoborohydride (25895-60-7) + ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt (848949-85-9) → (S)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4’-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid (875272-89-2)

Guidance literature:

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone; ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt; With potassium carbonate; In methanol; at 50 ℃; for 16h;

sodium cyanoborohydride; With methanol; at 50 ℃; for 4h;

Reference yield: 27.0%

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone (893407-18-6) + (S)-ethyl 2-amino-4-fluoro-4-methylpentanoate hydrochloride (2095926-24-0) → (S)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4’-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid (875272-89-2) + (S)-4-fluoro-4-methyl-2-(((R)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid

Guidance literature:

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone; (S)-ethyl 2-amino-4-fluoro-4-methylpentanoate hydrochloride; With potassium carbonate; In methanol;

With sodium tetrahydroborate; zinc(II) chloride; In 1,2-dimethoxyethane; acetonitrile;

DOI:10.1021/jacs.8b11027

Reference yield:

C21H20F4NO4S(1-)*K(1+) → (S)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4’-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid (875272-89-2)

Guidance literature:

With sodium tetrahydroborate; zinc(II) chloride; In 1,2-dimethoxyethane; at -10 ℃; for 1h;

C₂₁H₂₀F₄NO₄S^(1-)*K⁽¹⁺⁾; In methanol; 1,2-dimethoxyethane; acetonitrile; at -5 - 5 ℃; for 1.5h;

With hydrogenchloride; In methanol; 1,2-dimethoxyethane; tert-butyl methyl ether; water; acetone; acetonitrile; at 20 ℃; for 0.5h;

upstream raw materials:

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone

sodium cyanoborohydride

ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt

4-(4-bromophenyl)bromobenzene

Downstream raw materials:

(2S)-4-fluoro-4-methyl-2-({(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}amino)pentanoic acid dicyclohexylamine salt

Refernces

• 1、 -. "CATHEPSIN INHIBITORS". . . Retrieved 2019/06/23.
• 2、 O'Shea, Paul D.,Chen, G-Yi,Gauvreau, Danny,Gosselin, Francis,Hughes, Greg,Nadeau, Christian,Volante, Ralph P.. "A practical enantioselective synthesis of odanacatib, a potent cathepsin K inhibitor, via triflate displacement of an α-Trifluoromethylbenzyl triflate". experimental part. p. 1605 - 1610. Retrieved 2009/08/19.