tert-butyl N-{2-[3,4-bis(benzyloxy)phenyl]ethyl}carbamate

Base Information

• Chemical Name: tert-butyl N-{2-[3,4-bis(benzyloxy)phenyl]ethyl}carbamate
• CAS No.: 300362-80-5
• Molecular Formula: C₂₇H₃₁NO₄
• Molecular Weight: 433.547
• Mol file: 300362-80-5.mol

Synonyms:N-tert-butoxycarbonyl-3,4-dibenzyloxyphenylethylamine

Chemical Property of tert-butyl N-{2-[3,4-bis(benzyloxy)phenyl]ethyl}carbamate

Chemical Property:

• Solubility.: Dichloromethane; Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-tert-Butoxycarbonyl-3,4-dibenzyloxyphenylethylamine is an intermediate used in the synthesis of S-(-)-Tretoquinol Hydrochloride (T798100), which belongs to the class of adrenergic inhalants, selective β-2-adrenoreceptor agonists. S-(-)-Tretoquinol is used in the treatment of obstructive airway diseases. S-(-)-Tretoquinol is a bronchodilator.

Technology Process of tert-butyl N-{2-[3,4-bis(benzyloxy)phenyl]ethyl}carbamate

There total 6 articles about tert-butyl N-{2-[3,4-bis(benzyloxy)phenyl]ethyl}carbamate 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: 93.0%

N-(tert-butoxycarbonyl)dopamine (37034-31-4) + benzyl bromide (100-39-0) → N-tert-butoxycarbonyl-3,4-dibenzyloxyphenylethylamine (300362-80-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere; Darkness;

DOI:10.1039/c5tb00340g

Reference yield:

dopamine hydrochloride (62-31-7) → N-tert-butoxycarbonyl-3,4-dibenzyloxyphenylethylamine (300362-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq.NaOH / dioxane / 0.17 h

1.2: 90 percent / dioxane / 20 h

2.1: 85 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

With sodium hydroxide; potassium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ja0464802

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-3,4-dibenzyloxyphenylethylamine (300362-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85.5 percent / TEA / methanol / 0.5 h

2: 77.6 percent / K₂CO₃ / acetone / 16 h

With TEA; potassium carbonate; In methanol; acetone;

DOI:10.1021/ja0442062

upstream raw materials:

N-(tert-butoxycarbonyl)dopamine

benzyl bromide

di-tert-butyl dicarbonate

dopamine hydrochloride

Downstream raw materials:

2-(3,4-bis (phenylmethoxy)phenyl)ethylamine hydrochloride

3-(3,4-bis(benzyloxy)phenethylcarbamoyl) propanoic acid

N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-succinamic acid methyl ester

N-[2-(3,4-bis-benzyloxyphenyl)ethyl]succinimic acid 2,5-dioxo-pyrrolidin-1-yl ester