L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6

Base Information

• Chemical Name: L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6
• CAS No.: 137650-15-8
• Molecular Formula: C17H25NO5
• Molecular Weight: 323.389
• Mol file: 137650-15-8.mol

Synonyms:L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6

Chemical Property of L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6

Chemical Property:

• PSA: 84.86000
• LogP: 3.00870

Purity/Quality:

99% ^*data from raw suppliers

Methyl(s)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6

There total 3 articles about L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6 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: 88.0%

4-bromo-3,5-dimethylphenol (7463-51-6) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate (137650-15-8)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With iodine; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

4-bromo-3,5-dimethylphenol; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; at 60 ℃; for 16h;

Reference yield: 56.0%

4-iodo-3,5-dimethylphenol (80826-86-4) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate (137650-15-8)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iodine; zinc; In N,N-dimethyl-formamide; at 110 ℃; for 2h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acsmedchemlett.5b00344

Reference yield:

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoate (137650-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 4 h / 20 °C / Inert atmosphere

2: iodine; zinc; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / N,N-dimethyl-formamide / 2 h / 110 °C / Inert atmosphere; Microwave irradiation

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iodine; triphenylphosphine; zinc; In dichloromethane; N,N-dimethyl-formamide; 1: |Appel Halogenation / 2: |Negishi Coupling;

DOI:10.1021/acsmedchemlett.5b00344

upstream raw materials:

4-iodo-3,5-dimethylphenol

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

N-tert-butyloxycarbonyl-L-serine methyl ester

4-bromo-3,5-dimethylphenol

Downstream raw materials:

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2,6-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

(S)-N-Boc-2,6-dimethyltyrosine

5-<1-amino-2-(4-hydroxy-2,6-dimethylphenyl)ethyl>-1,5-dihydro-3-methyl-1-(3-phenylpropyl)-2H-pyrrol-2-one hydrochloride

5(S)-amino-6-(4-hydroxy-2,6-dimethylphenyl)-N-(3-phenylpropyl)-3(E)-hexenamide hydrochloride

Refernces

• 1、 Bender, Aaron M.,Griggs, Nicholas W.,Gao, Chao,Trask, Tyler J.,Traynor, John R.,Mosberg, Henry I.. "Rapid Synthesis of Boc-2′,6′-dimethyl- l -tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics". supporting information. p. 1199 - 1203. Retrieved 2015/12/23.