(2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester

Base Information

• Chemical Name: (2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester
• CAS No.: 176536-76-8
• Molecular Formula: C₂₀H₂₈N₂O₄
• Molecular Weight: 360.453
• Mol file: 176536-76-8.mol

Synonyms:(2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester

Chemical Property of (2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester

There total 1 articles about (2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic 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: 5.0%

potassium tert-butylate (865-47-4) + (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate (57229-67-1) + 4-isopropoxy-2-phenylmethanesulfonyl-pyrimidine (497944-66-8) → tert-butyl (S)-1-((benzyloxy)carbonyl)-2-(1-(4-isopropoxypyrimidin-2-yl)-1H-indol-3-yl)ethylcarbamate (1207188-00-8) + (2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester (176536-76-8)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2009.11.077

Reference yield: 80.0%

(2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester (176536-76-8) → Boc-Trp-OH (13139-14-5)

Guidance literature:

With cerium(III) chloride; sodium iodide; In acetonitrile; for 1h; Heating;

DOI:10.1021/jo010010y

Reference yield:

(2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester (176536-76-8) → C13H15FN2O4

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

1.2: 24 h / 0 - 20 °C

2.1: hydrogenchloride / 1,4-dioxane; water / 1.5 h / 20 °C

3.1: rhIDO / 1 h / 37 °C / Enzymatic reaction

With hydrogenchloride; sodium hydride; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/ml500385d

upstream raw materials:

potassium tert-butylate

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate

4-isopropoxy-2-phenylmethanesulfonyl-pyrimidine

Downstream raw materials:

Boc-Trp-OH