[2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide

Base Information

• Chemical Name: [2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide
• CAS No.: 362495-82-7
• Molecular Formula: C₂₃H₃₂N₂O₄S
• Molecular Weight: 432.584
• Mol file: 362495-82-7.mol

Synonyms:[2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide

Chemical Property of [2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide

There total 1 articles about [2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide 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: 73.0%

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) + (2R)-2-methyl-1-(p-tolylsulfonyl)aziridine (177971-32-3) → [2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide (362495-82-7) + (2R,4R)-2-Methyl-4-(toluene-4-sulfonylamino)-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:

With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo0103571

Reference yield: 87.0%

[2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide (362495-82-7) → [2S,4R]-(-)-2-methyl-4-(p-toluenesulfonylamino)pentanoic acid (362495-92-9)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; Heating;

DOI:10.1021/jo0103571

Reference yield:

[2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide (362495-82-7) → [3S,5R]-(-)-3,5-dimethyl-1-(p-toluenesulfonyl)pyrrolidin-2-one

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / aq. H₂SO₄ / dioxane / Heating

2: 93 percent / conc. HCl / Heating

3: 75 percent / (Me₃Si)2NLi / tetrahydrofuran / -20 °C

With hydrogenchloride; sulfuric acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jo0103571

upstream raw materials:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

(2R)-2-methyl-1-(p-tolylsulfonyl)aziridine

Downstream raw materials:

[2S,4R]-(-)-2-methyl-4-(p-toluenesulfonylamino)pentanoic acid

[2S,4R]-(-)-methyl 2-methyl-4-(p-toluenesulfonylamino)pentanoate