N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

Base Information

Chemical Name:N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid
CAS No.:258530-42-6
Molecular Formula:C₃₈H₄₆N₆O₇
Molecular Weight:698.819
Hs Code.:

Synonyms:N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

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Chemical Property of N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

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Technology Process of N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

There total 9 articles about N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid 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: 93.0%

: 258530-41-5
N-[1-{1-[1-(benzyloxycarbonylamino-methyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-2-tert-butoxycarbonylamino-succinamic acid benzyl ester

: 258530-42-6
N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In water; N,N-dimethyl-formamide; for 6h;
DOI:10.1021/jm040832y

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 258530-42-6
N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

Guidance literature:: Multi-step reaction with 6 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: 69 percent / Et₃N / dimethylformamide / 4 h / 20 °C

6.1: 93 percent / H₂ / Pd/C / dimethylformamide; H₂O / 6 h

With hydrogenchloride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm040832y

Reference yield:

: 185384-16-1,179051-72-0
(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropylamine

: 258530-42-6
N-[1-(S)-[1-(S)-(2-amino-1-(R)-benzylethylcarbamoyl)-2-phenylethylcarbamoyl]-2-(1H-indol-3-yl)ethyl]-2-(R)-tert-butoxycarbonylaminosuccinic acid

Guidance literature:: Multi-step reaction with 8 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: 69 percent / Et₃N / dimethylformamide / 4 h / 20 °C

8.1: 93 percent / H₂ / Pd/C / dimethylformamide; H₂O / 6 h

With hydrogenchloride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm040832y