3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide

Base Information

• Chemical Name: 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide
• CAS No.: 282529-13-9
• Molecular Formula: C₃₇H₄₀N₆O₄
• Molecular Weight: 632.762
• Mol file: 282529-13-9.mol

Synonyms:

Chemical Property of 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide

There total 10 articles about 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide 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:

(S)-3-Methyl-2-[(S)-2-oxo-4-((S)-5-oxo-pyrrolidine-2-carbonyl)-3-(1-trityl-1H-imidazol-4-ylmethyl)-piperazin-1-yl]-butyric acid pentafluorophenyl ester → 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide (282529-13-9)

Guidance literature:

With ammonia; In ethanol; at 20 ℃; for 8h;

DOI:10.1002/(SICI)1522-2675(20000412)83:4<722::AID-HLCA722>3.0.CO;2-Z

Reference yield:

L-valine methylester hydrochloride (6306-52-1) → 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide (282529-13-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / BOP; Et₃N / CH₂Cl₂ / 12 h

2: 4-(aminomethyl)piperidine / CHCl₃ / 2 h

3: 93.6 percent / Et₃N / CHCl₃ / 5 h

4: 40 percent / K₂CO₃ / dimethylformamide / 14 h

5: 88.3 percent / K₂CO₃; PhSH / dimethylformamide / 12 h / 20 °C

6: 79 percent / BOP; Et₃N / CH₂Cl₂ / 48 h / 20 °C

7: LiOH / methanol; H₂O / 6 h / 20 °C

8: DCC; DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

9: 6.2 mg / NH₃ / ethanol / 8 h / 20 °C

With dmap; lithium hydroxide; ammonia; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-Aminomethylpiperidine; thiophenol; triethylamine; dicyclohexyl-carbodiimide; In methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; 1: Acylation / 2: deacylation / 3: Acylation / 4: Cyclization / 5: Substitution / 6: Acylation / 7: Hydrolysis / 8: Esterification / 9: Substitution;

DOI:10.1002/(SICI)1522-2675(20000412)83:4<722::AID-HLCA722>3.0.CO;2-Z

Reference yield:

Fmoc-His(Trt)-OH (109425-51-6) → 3-methyl-2-(2-oxo-4-[(5-oxopyrrolidin-2-yl)carbonyl]-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanamide (282529-13-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / BOP; Et₃N / CH₂Cl₂ / 12 h

2: 4-(aminomethyl)piperidine / CHCl₃ / 2 h

3: 93.6 percent / Et₃N / CHCl₃ / 5 h

4: 40 percent / K₂CO₃ / dimethylformamide / 14 h

5: 88.3 percent / K₂CO₃; PhSH / dimethylformamide / 12 h / 20 °C

6: 79 percent / BOP; Et₃N / CH₂Cl₂ / 48 h / 20 °C

7: LiOH / methanol; H₂O / 6 h / 20 °C

8: DCC; DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

9: 6.2 mg / NH₃ / ethanol / 8 h / 20 °C

With dmap; lithium hydroxide; ammonia; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-Aminomethylpiperidine; thiophenol; triethylamine; dicyclohexyl-carbodiimide; In methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; 1: Acylation / 2: deacylation / 3: Acylation / 4: Cyclization / 5: Substitution / 6: Acylation / 7: Hydrolysis / 8: Esterification / 9: Substitution;

DOI:10.1002/(SICI)1522-2675(20000412)83:4<722::AID-HLCA722>3.0.CO;2-Z

upstream raw materials:

L-valine methylester hydrochloride

Fmoc-His(Trt)-OH

methyl 3-methyl-2-(2-oxo-3-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}piperazin-1-yl)butanoate

methyl 3-methyl-2-{2-(4-nitrobenzenesulfonamido)-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanamido}butanoate