di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate

Base Information

• Chemical Name: di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate
• CAS No.: 1256384-76-5
• Molecular Formula: C₃₆H₄₂N₄O₄S₂
• Molecular Weight: 658.886
• Mol file: 1256384-76-5.mol

Synonyms:di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate

Chemical Property of di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate

There total 6 articles about di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate 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: 47.0%

tert-butyl (2S)-2-[5-(4-bromophenyl)-1,3-thiazol-2-yl]pyrrolidine-1-carboxylate (1256384-71-0) + tert-butyl (2S)-2-{5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-thiazol-2-yl}pyrrolidine-1-carboxylate (1256384-74-3) → di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate (1256384-76-5)

Guidance literature:

With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 80 ℃; for 18h; Inert atmosphere;

Reference yield:

tert-butyl (2S)-2-[5-(4-bromophenyl)-1,3-thiazol-2-yl]pyrrolidine-1-carboxylate (1256384-71-0) + (S)-2-(5-(4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)thiazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (1310694-79-1) → di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate (1256384-76-5)

Guidance literature:

With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 80 ℃; for 7h;

Reference yield:

y (1007881-98-2) → di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate (1256384-76-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Lawessons reagent / tetrahydrofuran / 6 h / Reflux

2: potassium acetate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere

3: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 18 h / 80 °C / Inert atmosphere

With Lawessons reagent; potassium acetate; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane;

upstream raw materials:

tert-butyl (2S)-2-[5-(4-bromophenyl)-1,3-thiazol-2-yl]pyrrolidine-1-carboxylate

(S)-2-(5-(4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl)thiazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

1-(tert-butoxycarbonyl)-L-proline

α-amino-4-bromoacetophenone hydrochloride

Downstream raw materials:

methyl [(2S)-1-{(2S)-2-[5-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1,3-thiazol-5-yl}biphenyl-4-yl)-1,3-thiazol-2-yl]pyrrolidin-1-yl}-3-methyl-1-oxobutan-2-yl]carbamate

5,5'-biphenyl-4,4'-diylbis{2-[(2S)-pyrrolidin-2-yl]-1,3-thiazole}

di-tert-butyl (biphenyl-4,4'-diylbis{1,3-thiazole-5,2-diyl-(2S)-pyrrolidine-2,1-diyl[(1R)-2-oxo-1-phenylethane-2,1-diyl]})biscarbamate

N,N’-(biphenyl-4,4'-diylbis{1,3-thiazole-5,2-diyl-(2S)-pyrrolidine-2,1-diyl[(1R)-2-oxo-1-phenylethane-2,1-diyl]})dicyclopropanecarboxamide