N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide

Base Information

• Chemical Name: N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide
• CAS No.: 1283116-60-8
• Molecular Formula: C₃₇H₃₆BrN₅O₅
• Molecular Weight: 710.627

Synonyms:N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide

Chemical Property of N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide

There total 15 articles about N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide 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: 76.0%

(S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanoic acid (1283116-58-4) + (S)-4-(2-amino-4-methylpentanamido)-N-benzyl-2-bromobenzamide hydrochloride → N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide (1283116-60-8)

Guidance literature:

(S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanoic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 0.166667h; Inert atmosphere;

(S)-4-(2-amino-4-methylpentanamido)-N-benzyl-2-bromobenzamide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2010.12.010

Reference yield: 63.0%

(S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanoic acid (1283116-58-4) + (S)-4-(2-amino-4-methylpentanamido)-N-benzyl-2-bromobenzamide (1283116-55-1) → N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide (1283116-60-8)

Guidance literature:

(S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanoic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 0.166667h; Inert atmosphere;

(S)-4-(2-amino-4-methylpentanamido)-N-benzyl-2-bromobenzamide; In N,N-dimethyl-formamide; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmc.2010.12.010

Reference yield:

2-bromo-4-nitrobenzoic acid (16426-64-5) → N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide (1283116-60-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 25 °C / Inert atmosphere

1.2: 4 h / 25 °C / Inert atmosphere

2.1: tin(II) chloride dihdyrate / ethyl acetate / 2 h / 70 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: 4-methyl-morpholine / tetrahydrofuran / 25 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 3 h / 25 °C / Inert atmosphere

5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 25 °C / Inert atmosphere

5.2: 4 h / 25 °C / Inert atmosphere

With 4-methyl-morpholine; tin(II) chloride dihdyrate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2010.12.010

upstream raw materials:

4-amino-N-benzyl-2-bromobenzamide

(S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanoic acid

(S)-4-(2-amino-4-methylpentanamido)-N-benzyl-2-bromobenzamide

(S)-benzyl 2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)-propanoate

Downstream raw materials:

methyl 2'-(benzylcarbamoyl)-5'-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-(phosphonooxy)phenyl)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-4-carboxylate

4-((S)-3-(((S)-1-((6-(benzylcarbamoyl)-3'-carbamoyl-[1,1'-biphenyl]-3-yl)amino)-4-methyl-1-oxopentan-2-yl)-amino)-2-(4-cyanobenzamido)-3-oxopropyl)phenyl dihydrogen phosphate

4-((S)-3-(((S)-1-((6-(benzylcarbamoyl)-3'-cyano-[1,1'-biphenyl]-3-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-2-(4-cyanobenzamido)-3-oxopropyl)phenyl dihydrogenphosphate

methyl 2'-(benzylcarbamoyl)-5'-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-(phosphonooxy)phenyl)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-3-carboxylate

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