[[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid

Base Information

• Chemical Name: [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid
• CAS No.: 628298-46-4
• Molecular Formula: C₂₂H₂₄Cl₃NO₅S
• Molecular Weight: 520.861
• Mol file: 628298-46-4.mol

Synonyms:[[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid

Chemical Property of [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid

There total 6 articles about [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid 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: 74.0%

rac-[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid (628298-45-3) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid (628298-46-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 - 20 ℃; for 15.5h;

DOI:10.1021/jo030192r

Reference yield:

4-Methylbenzyl chloride (104-82-5) → [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid (628298-46-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / NaI / 1,2-dimethoxy-ethane / 11 h

2.1: BuLi / hexane; tetrahydrofuran / 0.42 h / 0 °C

2.2: hexane; tetrahydrofuran / 13 h

2.3: 235 mg / NaBH₄ / methanol; ethyl acetate / 1.25 h / 0 °C

3.1: Me₃SiBr / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 224 mg / CH₂Cl₂ / 3 h

5.1: 91 percent / aq. NaOH / dioxane / 4 h

6.1: 74 percent / aq. NaOH / dioxane / 15.5 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; trimethylsilyl bromide; sodium iodide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; dichloromethane;

DOI:10.1021/jo030192r

Reference yield:

thioacetic acid S-(4-methylbenzyl) ester (628298-41-9) → [[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl](2,2,2-trichloroethoxycarbonyl)amino]acetic acid (628298-46-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.42 h / 0 °C

1.2: hexane; tetrahydrofuran / 13 h

1.3: 235 mg / NaBH₄ / methanol; ethyl acetate / 1.25 h / 0 °C

2.1: Me₃SiBr / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 224 mg / CH₂Cl₂ / 3 h

4.1: 91 percent / aq. NaOH / dioxane / 4 h

5.1: 74 percent / aq. NaOH / dioxane / 15.5 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; trimethylsilyl bromide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1021/jo030192r

upstream raw materials:

rac-[1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethylamino]acetic acid

2,2,2-Trichloroethyl chloroformate

4-Methylbenzyl chloride

thioacetic acid S-(4-methylbenzyl) ester

Downstream raw materials:

[[(benzylcarbamoylmethyl)carbamoyl]methyl][1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethyl]carbamic acid 2,2,2-trichloroethyl ester