N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester
• CAS No.: 699536-26-0
• Molecular Formula: C₁₆H₂₂INO₅
• Molecular Weight: 435.259
• Mol file: 699536-26-0.mol

Synonyms:N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester

Chemical Property of N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester

There total 1 articles about N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl 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:

Boc-Tyr-OH (3978-80-1) → N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester (699536-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodide; sodium hydroxide / methanol

1.2: 100 percent / aq. sodium hypochlorite / methanol / 2 h / 4 °C

2.1: 68 percent / dicyclohexylcarbodiimide; dimethylaminopyridine / 1 h / 20 °C

With dmap; sodium hydroxide; dicyclohexyl-carbodiimide; sodium iodide; In methanol;

DOI:10.1016/j.tetlet.2004.03.112

Reference yield: 90.0%

tetramethylstannane (594-27-4) + N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester (699536-26-0) → N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-methylphenyl)-L-alanine ethyl ester (699536-27-1)

Guidance literature:

N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester; With Pd₂(dibenzylideneacetone)2*CHCl₃; triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 70 ℃; for 0.166667h;

With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 20 - 70 ℃;

tetramethylstannane; In 1-methyl-pyrrolidin-2-one; at 70 ℃; for 144h; Further stages.;

DOI:10.1016/j.tetlet.2004.03.112

Reference yield: 78.3%

trimethylsilylacetylene (1066-54-2) + N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester (699536-26-0) → N-tert-butyloxylcarbonyl-3-trimethylsilylethynyl-L-tyrosine ethyl ester (1328942-21-7)

Guidance literature:

N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-iodophenyl)-L-alanine ethyl ester; With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; In tetrahydrofuran; for 0.166667h; Inert atmosphere;

trimethylsilylacetylene; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/ja203483j

upstream raw materials:

Boc-Tyr-OH

Downstream raw materials:

N-(tert-butyloxycarbonyl)-3-(4-hydroxy-3-methylphenyl)-L-alanine ethyl ester

N-tert-butyloxylcarbonyl-3-trimethylsilylethynyl-L-tyrosine ethyl ester

N-tert-butyloxylcarbonyl-O-allyl-3-trimethylsilylethynyl-L-tyrosine ethyl ester

N-tert-butyloxylcarbonyl-O-allyl-3-bromoethynyl-L-tyrosine ethyl ester