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

Base Information

• Chemical Name: methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate
• CAS No.: 121147-58-8
• Molecular Formula: C₂₀H₂₁ClN₂O₄S
• Molecular Weight: 420.917
• Mol file: 121147-58-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate 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: 100.0%

tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((E)-2-(4-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate (121147-35-1) → methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate (121147-58-8)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 0.5h;

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

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate (121147-58-8)

Guidance literature:

Multi-step reaction with 11 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

11: 100 percent / trifluoroacetic acid / H₂O / 0.5 h / 20 °C

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

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

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate (121147-58-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

2: 88.7 percent / dimethylsulfoxide / 90 °C

3: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C

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

5: 90.8 percent / sodium azide / dimethylsulfoxide / 90 °C

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

7: 9.13 g / pyridine / 5 h / 0 - 5 °C

8: 65.9 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

9: 23.3 percent / sodium hydride / tetrahydrofuran / 1 h / 0 - 5 °C

10: 100 percent / trifluoroacetic acid / H₂O / 0.5 h / 20 °C

With sodium azide; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 9: Wittig reaction;

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

upstream raw materials:

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

L-4-hydroxyproline methyl ester hydrochloride

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

Downstream raw materials:

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