(2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide

Base Information

• Chemical Name: (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide
• CAS No.: 193807-60-2
• Molecular Formula: C₂₁H₂₀N₂O₄S
• Molecular Weight: 396.467
• Mol file: 193807-60-2.mol

Synonyms:

Chemical Property of (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide

Chemical Property:

• Melting Point: 169-170 °C
• Density: 1.309±0.06 g/cm3(Predicted)

Purity/Quality:

≥98% ^*data from raw suppliers

MMP-2/MMP-9InhibitorII ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: MMP-2/MMP-9 Inhibitor II is a potent inhibitor of MMP-2 and MMP-9.

Technology Process of (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide

There total 8 articles about (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide 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: 84.0%

(R)-N-Benzyloxy-2-(biphenyl-4-sulfonylamino)-3-phenyl-propionamide (193810-35-4) → (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide (193807-60-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 3.5h;

DOI:10.1021/jm9707582

Reference yield: 60.0%

C26H27NO5S → (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide (193807-60-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 4h;

DOI:10.1002/chem.201300817

Reference yield:

([1,1'-biphenyl]-4-ylsulfonyl)-D-phenylalanine (193807-58-8) → (2R)-[(4-biphenylylsulfonyl)amino]-N-hydroxy-3-phenylpropionamide (193807-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / HOBt*H₂O, N-methylmorpholine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide*HCl / dimethylformamide / 6 h / Ambient temperature

2: 84 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 3.5 h

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm9707582

upstream raw materials:

(R)-N-Benzyloxy-2-(biphenyl-4-sulfonylamino)-3-phenyl-propionamide

4-diphenylsulfonyl chloride

(R)-2-(Biphenyl-4-sulfonylamino)-3-phenyl-propionic acid benzyl ester

([1,1'-biphenyl]-4-ylsulfonyl)-D-phenylalanine

Refernces

• 1、 Tamura, Yoshinori,Watanabe, Fumihiko,Nakatani, Takuji,Yasui, Ken,Fuji, Masahiro,Komurasaki, Tadafumi,Tsuzuki, Hiroshige,Maekawa, Ryuji,Yoshioka, Takayuki,Kawada, Kenji,Sugita, Kenji,Ohtani, Mitsuaki. "Highly selective and orally active inhibitors of type IV collagenase (MMP-9 and MMP-2): N-sulfonylamino acid derivatives". . p. 640 - 649. Retrieved 2007/10/03.