2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

Base Information

Chemical Name:2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide
CAS No.:166446-82-8
Molecular Formula:C₃₇H₅₀N₆O₄
Molecular Weight:642.842
Hs Code.:

Synonyms:2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

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Chemical Property of 2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

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Technology Process of 2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

There total 8 articles about 2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide 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: 90.0%

: 166446-76-0
2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(azidomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

: 166446-82-8
2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; for 15h;
DOI:10.1021/jm00017a022

Reference yield:

: 13734-28-6
Boc-Lys-OH

: 166446-82-8
2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / 1 N aq. NaOH / 15 h

2: 1.) isobutyl chloroformate, diisopropylethylamine, 2.) lithium aluminum hydride / 1.) THF, 0 deg C, 1 h, 2.) THF, Et₂O, RT, 24 h

3: 46 percent / DMAP, triethylamine / CH₂Cl₂ / 2.25 h / Ambient temperature

4: 69 percent / sodium azide / dimethylformamide / 1.5 h / 80 °C

5: 100 percent / 4 N HCl / dioxane / 15 h / Ambient temperature

6: 68 percent / triethylamine, N-hydroxysuccinimide, ethylcarbodiimide hydrochloride / CH₂Cl₂ / 15 h / Ambient temperature

7: 90 percent / H₂ / 10percent Pd/C / ethanol / 15 h

With hydrogenchloride; dmap; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; sodium azide; 3-ethylcarbodiimide hydrochloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00017a022

Reference yield:

: 614-68-6
2-tolyl isocyanate

: 166446-82-8
2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<1-(S)-(aminomethyl)-5-(3-o-tolylureido)pentyl>-3-(1H-indol-3-yl)-2-(S)-methylpropionamide

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / 1 N aq. NaOH / 15 h

2: 1.) isobutyl chloroformate, diisopropylethylamine, 2.) lithium aluminum hydride / 1.) THF, 0 deg C, 1 h, 2.) THF, Et₂O, RT, 24 h

3: 46 percent / DMAP, triethylamine / CH₂Cl₂ / 2.25 h / Ambient temperature

4: 69 percent / sodium azide / dimethylformamide / 1.5 h / 80 °C

5: 100 percent / 4 N HCl / dioxane / 15 h / Ambient temperature

6: 68 percent / triethylamine, N-hydroxysuccinimide, ethylcarbodiimide hydrochloride / CH₂Cl₂ / 15 h / Ambient temperature

7: 90 percent / H₂ / 10percent Pd/C / ethanol / 15 h

With hydrogenchloride; dmap; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; sodium azide; 3-ethylcarbodiimide hydrochloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00017a022