N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide

Base Information

• Chemical Name: N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide
• CAS No.: 502937-01-1
• Molecular Formula: C₇₀H₁₀₇N₉O₁₄
• Molecular Weight: 1298.67
• Mol file: 502937-01-1.mol

Synonyms:N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide

Chemical Property of N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide

There total 17 articles about N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide 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: 67.0%

N-[(2-tert-butyloxycarbonyl)-2-adamantyl] [(2S)-2-amino-3-(4-tert-butyloxyphenyl)]propanamide (502937-09-9) + 1-{[6-N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxylic acid (502937-00-0) → N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide (502937-01-1)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/S0968-0896(02)00342-5

Reference yield:

2-amino-2-adamantanecarboxylic acid (42381-05-5) → N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide (502937-01-1)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. KOH

2: 49 percent / toluene / 10 h / 110 °C

3: 91 percent / H₂; AcOH / 10 percent Pd/C / methanol / 12 h / 20 °C

4: 92 percent / DCC; HOBt / dimethylformamide / 12 h / 20 °C

5: 90 percent / piperidine / tetrahydrofuran / 1.5 h / 20 °C

6: 67 percent / DCC; HOBT / dimethylformamide / 12 h / 20 °C

With piperidine; potassium hydroxide; hydrogen; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(02)00342-5

Reference yield:

5-(tert-butyldimethyl-silyloxy)pentan-1-ol (83067-20-3) → N-{(2S)-1-[2-(tert-butyloxycarbonyl)adamantyl-2-amino]-3-(4-tert-butyloxyphenyl)-1-oxo-propan-2-yl} 1-{6-[N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxamide (502937-01-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / PPh₃; DEAD / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2: 58 percent / MeONa / methanol / 0 - 20 °C

3: 67 percent / toluene / 8 h / Heating

4: 85 percent / K₂CO₃; 18-crown-6 / acetonitrile / 12 h / 70 °C

5: 86 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

6: 90 percent / PPh₃; HN₃; DEAD / CH₂Cl₂ / 0.5 h / 20 °C

7: 99 percent / 4N KOH / methanol; tetrahydrofuran / 12 h / 20 °C

8: 97 percent / conc. HCl; H₂ / 10 percent Pd/C / methanol; ethyl acetate / 12 h / 20 °C

9: 71 percent / Triton-B / dimethylsulfoxide; methanol / 72 h / 20 °C

10: 67 percent / DCC; HOBT / dimethylformamide / 12 h / 20 °C

With hydrogenchloride; potassium hydroxide; 18-crown-6 ether; tris-(2-chloro-ethyl)-amine; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; N-benzyl-trimethylammonium hydroxide; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0968-0896(02)00342-5

upstream raw materials:

N-[(2-tert-butyloxycarbonyl)-2-adamantyl] [(2S)-2-amino-3-(4-tert-butyloxyphenyl)]propanamide

1-{[6-N,N'-bis(tert-butyloxycarbonyl)guanidino]hexyl}-6-{[5-N,N'-bis(tert-butyloxycarbonyl)guanidino]pentyloxy}indole-2-carboxylic acid

2-amino-2-adamantanecarboxylic acid

5-(tert-butyldimethyl-silyloxy)pentan-1-ol