tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate
• CAS No.: 121147-35-1
• Molecular Formula: C₂₅H₂₉ClN₂O₆S
• Molecular Weight: 521.034
• Mol file: 121147-35-1.mol

Synonyms:tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate

Chemical Property of tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate

There total 12 articles about tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate 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: 23.3%

triphenyl-(4-methoxycarbonylbenzyl)phosphonium chloride (1253-47-0) + tert-butyl (2S,4R)-2-formyl-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidine-1-carboxylate (121148-09-2) → tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((Z)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate (121147-37-3) + tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate (121147-35-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 5 ℃; for 1h;

DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate (121147-35-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 53.4 g / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

2: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 88.7 percent / dimethylsulfoxide / 90 °C

4: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C

5: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 90.8 percent / sodium azide / dimethylsulfoxide / 90 °C

7: H₂ / 10 percent Pd/C / methanol / 3 h / 20 °C / 2280 Torr

8: 9.13 g / pyridine / 5 h / 0 - 5 °C

9: 65.9 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

10: 23.3 percent / sodium hydride / tetrahydrofuran / 1 h / 0 - 5 °C

With sodium azide; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene; 10: Wittig reaction;

DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate (121147-35-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 53.4 g / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

2: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 88.7 percent / dimethylsulfoxide / 90 °C

4: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C

5: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 90.8 percent / sodium azide / dimethylsulfoxide / 90 °C

7: H₂ / 10 percent Pd/C / methanol / 3 h / 20 °C / 2280 Torr

8: 9.13 g / pyridine / 5 h / 0 - 5 °C

9: 65.9 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

10: 23.3 percent / sodium hydride / tetrahydrofuran / 1 h / 0 - 5 °C

With sodium azide; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene; 10: Wittig reaction;

DOI:10.1016/S0968-0896(01)00397-2

upstream raw materials:

triphenyl-(4-methoxycarbonylbenzyl)phosphonium chloride

tert-butyl (2S,4R)-2-formyl-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

(2S,4R)-1-(4-Chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(E)-2-(4-methoxycarbonylphenyl)vinyl]pyrrolidine