tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate
• CAS No.: 1269615-33-9
• Molecular Formula: C₃₃H₃₇N₅O₄
• Molecular Weight: 567.688
• Mol file: 1269615-33-9.mol

Synonyms:tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate

There total 20 articles about tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-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:

1-(3-phenyl-1H-1,2,4-triazol-5-yl)methanamine (805179-91-3) + 4-(((2S,5R)-1-(tert-butoxycarbonyl)-5-((R)-hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)benzoic acid (1269429-01-7) → tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate (1269615-33-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

Reference yield:

1,4-bromoiodobenzene (589-87-7) → tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate (1269615-33-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; copper(l) iodide / N,N-dimethyl-formamide / 6 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3.1: platinum(II) chloride / toluene / 6 h / 80 °C / Inert atmosphere

4.1: sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

6.1: triethylamine / palladium diacetate / 120 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

8.1: water; lithium hydroxide / methanol / 20 °C

8.2: pH 4.5

9.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 20 °C

With tetrabutyl ammonium fluoride; water; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; platinum(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

tert-butyl (4S,5R)-4-formyl-2,2-dimethyl-5-phenyloxazolidine-3-carboxylate → tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-[4-({[(3-phenyl-1H-1,2,4-triazol-5-yl)methyl]amino}carbonyl)benzyl]pyrrolidine-1-carboxylate (1269615-33-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: dichloromethane / 40 h / 20 °C

2.1: hydrogen / palladium 10% on activated carbon / acetone / 24 h / 20 °C

3.1: sodium t-butanolate / dimethyl sulfoxide / 0.75 h / 20 °C

3.2: 1.5 h / 20 °C

4.1: acetyl chloride; methanol / 5 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4.5 h / -78 - 20 °C

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

8.1: triphenylphosphine / palladium diacetate / ethanol / Inert atmosphere; Reflux

9.1: hydrogen / palladium 10% on activated carbon / ethanol / 50 °C

10.1: tetrahydrofuran / 20 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

12.1: water; lithium hydroxide / methanol / 20 °C

12.2: pH 4.5

13.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 20 °C

With methanol; tetrabutyl ammonium fluoride; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hydroxide; sodium t-butanolate; palladium 10% on activated carbon; palladium diacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

upstream raw materials:

1,4-bromoiodobenzene

4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

tert-butyl (4R,5R)-4-{4-[4-(methoxycarbonyl)phenyl]but-3-en-1-yl}-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

1-(3-phenyl-1H-1,2,4-triazol-5-yl)methanamine