3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid

Base Information

• Chemical Name: 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid
• CAS No.: 695215-96-4
• Molecular Formula: C₁₈H₁₉FN₂O₅S
• Molecular Weight: 394.424
• Mol file: 695215-96-4.mol

Synonyms:3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid

Chemical Property of 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid

There total 6 articles about 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic 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: 80.0%

N-[1-(4-fluoro-phenyl)-ethyl]-5-(methanesulfonyl-methyl-amino)-isophthalamic acid methyl ester (827579-70-4) → 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid (695215-96-4)

Guidance literature:

N-[1-(4-fluoro-phenyl)-ethyl]-5-(methanesulfonyl-methyl-amino)-isophthalamic acid methyl ester; With water; sodium hydroxide; In methanol; at 20 ℃; for 2h;

With hydrogenchloride; In methanol; water;

Reference yield:

3-(methoxycarbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid (695215-94-2) → 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid (695215-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / EDC; HOAt / CHCl₃ / 50 h / 20 °C

2: aq. LiOH / tetrahydrofuran / 5 h / 20 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; chloroform;

DOI:10.1021/jm061046r

Reference yield:

dimethyl 5-aminoisophthalate (99-27-4) → 3-({[(1R)-1-(4-fluorophenyl)ethyl]amino}carbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid (695215-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

2: 98 percent / NaH / dimethylformamide / 1 h

3: 82 percent / aq. NaOH / tetrahydrofuran; methanol / 8 h / 0 - 20 °C

4: BOP; diisopropylamine / CH₂Cl₂ / 20 °C

5: aq. NaOH / methanol; tetrahydrofuran / 50 °C

With pyridine; sodium hydroxide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm049379g

upstream raw materials:

N-[1-(4-fluoro-phenyl)-ethyl]-5-(methanesulfonyl-methyl-amino)-isophthalamic acid methyl ester

3-(methoxycarbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid

dimethyl 5-aminoisophthalate

dimethyl-5-[methyl(methylsulfonyl)amino]isophthalate

Downstream raw materials:

N-(1-benzyl-3-cyclopropylamino-2-hydroxy-propyl)-N'-[1-(4-fluoro-phenyl)-ethyl]-5-(methanesulfonyl-methyl-amino)-isophthalamide