[(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 200864-65-9
• Molecular Formula: C₂₄H₂₉N₃O₄
• Molecular Weight: 423.512

Synonyms:[(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

There total 2 articles about [(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl 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: 94.0%

tyrosamine (51-67-2) + Boc-Trp-OH (13139-14-5) → [(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (200864-65-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1002/adsc.201701016

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → [(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (200864-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; tetrahydrofuran / 19 h / 20 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 4 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1002/adsc.201701016

Reference yield: 100.0%

[(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (200864-65-9) → (S)-2-Amino-N-[2-(4-hydroxy-phenyl)-ethyl]-3-(1H-indol-3-yl)-propionamide; hydrochloride

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; for 4h; Ambient temperature;

DOI:10.1021/jm970494j

upstream raw materials:

tyrosamine

Boc-Trp-OH

di-tert-butyl dicarbonate

L-Tryptophan

Downstream raw materials:

(R)-3-[(S)-1-[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethylcarbamoyl]-5-methyl-hexanoic acid methyl ester

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