N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

Base Information

• Chemical Name: N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester
• CAS No.: 1026301-23-4
• Molecular Formula: C₅₃H₅₈N₆O₉
• Molecular Weight: 923.078
• Mol file: 1026301-23-4.mol

Synonyms:N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

Chemical Property of N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

There total 9 articles about N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester 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:

4-benzyl Boc-D-aspartate (51186-58-4,98482-77-0) + (2-(R)-{2-(S)-[2-(S)-amino-3-(1H-indol-3-yl)propionylamino]-3-phenylpropionylamino}-3-phenylpropyl)carbamic acid benzyl ester (211689-64-4) → N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester (1026301-23-4)

Guidance literature:

4-benzyl Boc-D-aspartate; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 0.25h;

(2-(R)-{2-(S)-[2-(S)-amino-3-(1H-indol-3-yl)propionylamino]-3-phenylpropionylamino}-3-phenylpropyl)carbamic acid benzyl ester; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/jm040832y

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester (1026301-23-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HOBt; EDC*HCl / acetonitrile / 0.5 h / 0 °C

1.2: Et₃N / acetonitrile / 3 h / 20 °C

2.1: 30 g / HCl / methanol; dioxane / 8 h / 20 °C

3.1: HOBt; EDC*HCl / dimethylformamide / 0.25 h

3.2: Et₃N / dimethylformamide / 2 h / 20 °C

4.1: HCl / methanol; dioxane / 5.5 h / 20 °C

5.1: HOBt; EDC*HCl / dimethylformamide / 0.25 h

5.2: Et₃N / dimethylformamide / 4 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm040832y

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid benzyl ester (1026301-23-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / HCl / methanol; dioxane / 1 h

3.1: HOBt; EDC*HCl / acetonitrile / 0.5 h / 0 °C

3.2: Et₃N / acetonitrile / 3 h / 20 °C

4.1: 30 g / HCl / methanol; dioxane / 8 h / 20 °C

5.1: HOBt; EDC*HCl / dimethylformamide / 0.25 h

5.2: Et₃N / dimethylformamide / 2 h / 20 °C

6.1: HCl / methanol; dioxane / 5.5 h / 20 °C

7.1: HOBt; EDC*HCl / dimethylformamide / 0.25 h

7.2: Et₃N / dimethylformamide / 4 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm040832y

upstream raw materials:

4-benzyl Boc-D-aspartate

(2-(R)-{2-(S)-[2-(S)-amino-3-(1H-indol-3-yl)propionylamino]-3-phenylpropionylamino}-3-phenylpropyl)carbamic acid benzyl ester

N-tert-butoxycarbonyl-L-phenylalanine

benzyl chloroformate

Downstream raw materials:

(2S,5S,8R,13R)-13-Amino-5,8-dibenzyl-2-(1H-indol-3-ylmethyl)-1,4,7,10-tetraaza-cyclotetradecane-3,6,11,14-tetraone

[(3R,6S,9S,12R)-3,6-Dibenzyl-9-(1H-indol-3-ylmethyl)-5,8,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-carbamic acid tert-butyl ester

N-[1-[1-(1-aminomethyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-3-tert-butoxycarbonylamino-succinamic acid