methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

Base Information

Chemical Name:methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate
CAS No.:121147-40-8
Molecular Formula:C₂₀H₂₁ClN₂O₄S
Molecular Weight:420.917
Hs Code.:

Synonyms:methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

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Chemical Property of methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

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Technology Process of methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

There total 12 articles about methyl 3-((Z)-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: 91.4%

: 121147-38-4
tert-butyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-2-((Z)-2-(3-(methoxycarbonyl)phenyl)ethenyl)-1-pyrrolidinecarboxylate

: 121147-40-8
methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 0.5h;
DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 121147-40-8
methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

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

11: 91.4 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:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 121147-40-8
methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate

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

10: 91.4 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