N-tert-Butoxycarbonyl 3,5-Diiodotyramine

Base Information

• Chemical Name: N-tert-Butoxycarbonyl 3,5-Diiodotyramine
• CAS No.: 788824-51-1
• Molecular Formula: C13H17I2NO3
• Molecular Weight: 489.092
• DSSTox Substance ID: DTXSID60468723
• Mol file: 788824-51-1.mol

Synonyms:N-tert-Butoxycarbonyl 3,5-Diiodotyramine;788824-51-1;tert-butyl N-[2-(4-hydroxy-3,5-diiodophenyl)ethyl]carbamate;n-t-boc-3,5-diiodotyramine;SCHEMBL4453472;DTXSID60468723;N-(tert-Butoxycarbonyl)[2-(3,5-diiodo-4-hydroxyphenyl)ethyl]amine;2-(4-Hydroxy-3,5-diiodophenyl)ethyl]carbamic Acid 1,1-Dimethylethyl Ester;AKOS015965516;FT-0664003

Chemical Property of N-tert-Butoxycarbonyl 3,5-Diiodotyramine

Chemical Property:

• Melting Point: 111-118°C
• Boiling Point: 435.5±45.0 °C(Predicted)
• PKA: 7.16±0.25(Predicted)
• PSA: 62.05000
• Density: 1.883±0.06 g/cm3(Predicted)
• LogP: 3.87300
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 488.92979
• Heavy Atom Count: 19
• Complexity: 295

Purity/Quality:

95% ^*data from raw suppliers

N-tert-Butoxycarbonyl 3,5-diiodotyramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCC1=CC(=C(C(=C1)I)O)I

Technology Process of N-tert-Butoxycarbonyl 3,5-Diiodotyramine

There total 4 articles about N-tert-Butoxycarbonyl 3,5-Diiodotyramine 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: 92.0%

N-t-butoxycarbonyl-tyramine (64318-28-1) → tert-butyl (4-hydroxy-3,5-diiodophenethyl)carbamate (788824-51-1)

Guidance literature:

With Iodine monochloride; N-butylamine; In tetrahydrofuran; at -35 - 0 ℃; for 3h;

DOI:10.1021/jm0505718

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (4-hydroxy-3,5-diiodophenethyl)carbamate (788824-51-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / aq. NaHCO₃ / tetrahydrofuran / 24 h

2: 92 percent / ICl; BuNH₂ / tetrahydrofuran / 3 h / -35 - 0 °C

With Iodine monochloride; sodium hydrogencarbonate; N-butylamine; In tetrahydrofuran;

DOI:10.1021/jm0505718

Reference yield:

tyrosamine (51-67-2) → tert-butyl (4-hydroxy-3,5-diiodophenethyl)carbamate (788824-51-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; 1,4-dioxane / 2 h / 0 °C / pH Ca_. 10

2: iodine; dihydrogen peroxide / water / 50 °C

With dihydrogen peroxide; iodine; sodium hydroxide; In 1,4-dioxane; water;

upstream raw materials:

N-t-butoxycarbonyl-tyramine

tyrosamine

di-tert-butyl dicarbonate

Downstream raw materials:

3,5-Diiodothyronamine

tert-butyl 3,5-diiodo-4-(4-methoxyphenoxy)phenethylcarbamate

3,5-Diiodotyramine

3-Iodothyronamine

Refernces

• 1、 -. "A solution for detecting metal ion content of organic compound and use thereof". Paragraph 0064; 0176; 0177; 0178. . Retrieved 2017/09/26.
• 2、 Mondal, Santanu,Mugesh, Govindasamy. "Regioselective deiodination of iodothyronamines, endogenous thyroid hormone derivatives, by deiodinase mimics". supporting information. p. 11120 - 11128,9. Retrieved 2014/11/27.