(2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid

Base Information

• Chemical Name: (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid
• CAS No.: 193980-00-6
• Molecular Formula: C₁₇H₁₉NO₄S
• Molecular Weight: 333.408
• Mol file: 193980-00-6.mol

Synonyms:(2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid

Chemical Property of (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid

There total 12 articles about (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic 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:

(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide (943241-46-1) → (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid (193980-00-6)

Guidance literature:

With potassium hydroxide; In ethanol; at 80 ℃; for 48h;

DOI:10.1021/ol0708166

Reference yield:

benzaldehyde (100-52-7) → (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid (193980-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 77 percent / Ti(OEt)4 / CH₂Cl₂ / cooling

2.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: tetrahydrofuran / -78 °C

3.1: HCl / methanol; diethyl ether / 0.5 h / 0 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

5.1: aq. KOH / ethanol / 48 h / 80 °C

With hydrogenchloride; dmap; potassium hydroxide; triethylamine; lithium hexamethyldisilazane; titanium(IV) tetraethanolate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ol0708166

Reference yield:

(4S,5R)-4-methyl-3-<(2R,3R)-2-methyl-3-phenyl-3-(tosylamino)propionyl>-5-phenyloxazolidin-2-one (165036-40-8) → (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid (193980-00-6)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(01)89406-0

upstream raw materials:

(4S,5R)-4-methyl-3-<(2R,3R)-2-methyl-3-phenyl-3-(tosylamino)propionyl>-5-phenyloxazolidin-2-one

N-(benzylidene)-p-methylbenzenesulfonamide

2-propanoyl-3-phenyl-l-menthopyrazole

(1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide

Downstream raw materials:

(3R,4R)-3-methyl-4-phenylazetidin-2-one

(3R,4R)-3-methyl-4-phenyl-1-tosylazetidin-2-one