(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

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Chemical Name:(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid
CAS No.:454474-29-4
Molecular Formula:C₂₂H₃₂N₂O₆S
Molecular Weight:452.572
Hs Code.:

Synonyms:(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

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Chemical Property of (5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

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Technology Process of (5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

There total 12 articles about (5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic 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: 68.5%

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 121148-21-8
tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

: 454474-29-4
(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

Guidance literature:: With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 6h;
DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

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

: 454474-29-4
(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

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: 5.38 g / pyridine / 5 h / 0 - 5 °C

9: 74 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

10: 68.5 percent / sodium hydride / dimethylsulfoxide / 6 h / 20 °C

With sodium azide; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene; 10: Wittig reaction;
DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 454474-29-4
(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid

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: 5.38 g / pyridine / 5 h / 0 - 5 °C

9: 74 percent / diisobutylaluminum hydride / toluene / 5 h / -78 °C

10: 68.5 percent / sodium hydride / dimethylsulfoxide / 6 h / 20 °C

With sodium azide; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene; 10: Wittig reaction;
DOI:10.1016/S0968-0896(01)00397-2