N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine

Base Information

• Chemical Name: N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine
• CAS No.: 251317-75-6
• Molecular Formula: C₂₉H₄₃N₅O₄
• Molecular Weight: 525.692

Synonyms:N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine

Chemical Property of N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine

There total 6 articles about N¹-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine 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: 32.0%

2-(o-azidophenyl)propylamin (146954-29-2) + 1-[5-(t-butoxycarbonyl)amino-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-pentyl] methanesulfonate (251317-74-5) → N1-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N5-(o-azido-phenethyl)-1,5-pentanediamine (251317-75-6)

Guidance literature:

In acetonitrile; at 60 ℃; for 7h;

DOI:10.1016/S0968-0896(99)00104-2

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N1-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N5-(o-azido-phenethyl)-1,5-pentanediamine (251317-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

2: 94 percent / Et₃N / diethyl ether / 1.5 h / -20 °C

3: 32 percent / acetonitrile / 7 h / 60 °C

With triethylamine; In tetrahydrofuran; diethyl ether; acetonitrile; 1: Acylation / 2: Substitution / 3: Substitution;

DOI:10.1016/S0968-0896(99)00104-2

Reference yield:

2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile (20850-49-1) → N1-t-butoxycarbonyl-2-(3,4-dimethoxyphenyl)-2-isopropyl-N5-(o-azido-phenethyl)-1,5-pentanediamine (251317-75-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / LDA / tetrahydrofuran; hexane / -50 - 20 °C

2: 75 percent / LiAlH₄; AlCl₃ / diethyl ether / 16 h / 20 °C

3: 81 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

4: 94 percent / Et₃N / diethyl ether / 1.5 h / -20 °C

5: 32 percent / acetonitrile / 7 h / 60 °C

With lithium aluminium tetrahydride; aluminium trichloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; acetonitrile; 1: Substitution / 2: Reduction / 3: Acylation / 4: Substitution / 5: Substitution;

DOI:10.1016/S0968-0896(99)00104-2

upstream raw materials:

2-(o-azidophenyl)propylamin

1-[5-(t-butoxycarbonyl)amino-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-pentyl] methanesulfonate

di-tert-butyl dicarbonate

2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile

Downstream raw materials:

2-(3,4-dimethoxyphenyl)-2-isopropyl-N⁵-(o-azido-phenethyl)-1,5-pentanediamine

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