L-Tyrosine, N-acetyl-3,5-diiodo-O-(4-methoxyphenyl)-, ethyl ester

Base Information

• Chemical Name: L-Tyrosine, N-acetyl-3,5-diiodo-O-(4-methoxyphenyl)-, ethyl ester
• CAS No.: 83249-56-3
• Molecular Formula: C20H21I2NO5
• Molecular Weight: 609.199
• Hs Code.: 2924299090
• European Community (EC) Number: 815-708-2
• Nikkaji Number: J963.053H
• Mol file: 83249-56-3.mol

Synonyms:SCHEMBL8745456;LCJKMEUFNHSFPB-SFHVURJKSA-N;L-Tyrosine, N-acetyl-3,5-diiodo-O-(4-methoxyphenyl)-, ethyl ester;(S)-N-acetyl-3,5-diiodo-4-p-methoxyphenoxyphenylalanine ethyl ester;N-Acetyl-3,5-diiodo-4-(4-methoxyphenoxy)-L-phenylalanine ethyl ester

Chemical Property of L-Tyrosine, N-acetyl-3,5-diiodo-O-(4-methoxyphenyl)-, ethyl ester

Chemical Property:

• Vapor Pressure: 9.97E-15mmHg at 25°C
• Refractive Index: 1.614
• Boiling Point: 608 °C at 760 mmHg
• Flash Point: 321.5 °C
• PSA: 73.86000
• Density: 1.724g/cm³
• LogP: 4.69790
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 608.95092
• Heavy Atom Count: 28
• Complexity: 501

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl2-acetamido-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CC(=C(C(=C1)I)OC2=CC=C(C=C2)OC)I)NC(=O)C
• Isomeric SMILES: CCOC(=O)[C@H](CC1=CC(=C(C(=C1)I)OC2=CC=C(C=C2)OC)I)NC(=O)C

Technology Process of L-Tyrosine, N-acetyl-3,5-diiodo-O-(4-methoxyphenyl)-, ethyl ester

There total 12 articles about L-Tyrosine, N-acetyl-3,5-diiodo-O-(4-methoxyphenyl)-, 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: 89.7%

4-methoxyphenylboronic acid (5720-07-0) + N-acetyl-3,5-diiodo-L-tyrosine ethyl ester (21959-36-4) → N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester (83249-56-3)

Guidance literature:

4-methoxyphenylboronic acid; N-acetyl-3,5-diiodo-L-tyrosine ethyl ester; With copper(II) perchlorate hexahydrate; In dichloromethane; at 25 ℃; for 0.166667h;

With pyridine; In dichloromethane; at 25 ℃; for 3h; Reagent/catalyst;

Reference yield:

3,5-diiodo-l-tyrosine (300-39-0) → N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester (83249-56-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / water / 0 - 15 °C

2.1: 0.5 h / 20 °C

2.2: 1 h / 20 - 50 °C

3.1: copper(II) perchlorate hexahydrate / dichloromethane / 0.17 h / 25 °C

3.2: 3 h / 25 °C

With copper(II) perchlorate hexahydrate; sodium hydroxide; In dichloromethane; water;

Reference yield:

N-acetyl-3,5-diiodo-L-tyrosine (1027-28-7) → N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester (83249-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 0.5 h / 20 °C

1.2: 1 h / 20 - 50 °C

2.1: copper(II) perchlorate hexahydrate / dichloromethane / 0.17 h / 25 °C

2.2: 3 h / 25 °C

With copper(II) perchlorate hexahydrate; In dichloromethane;

upstream raw materials:

ethanol

N-acetyl-3,5-diiodo-O'-methyl-L-thyronine

N-acetyl-3,5-diiodo-L-tyrosine ethyl ester

4,4'-dimethoxy-diphenyliodonium bromide

Downstream raw materials:

N-acetyl-3,5-dicyano-O'-methyl-L-thyronine ethyl ester

N-acetyl-3,5-diiodo-O'-methyl-3',5'-dinitro-L-thyronine ethyl ester

2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid

N-acetyl-3,5-diiodo-O'-methyl-L-thyronine

Refernces

• 1、 Evans, David A.,Katz, Jeffrey L.,West, Theodore R.. "Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine". . p. 2937 - 2940. Retrieved 2007/10/03.