methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate

Base Information

• Chemical Name: methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate
• CAS No.: 1607804-26-1
• Molecular Formula: C₂₆H₄₀INO₁₀
• Molecular Weight: 653.509
• Mol file: 1607804-26-1.mol

Synonyms:methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate

Chemical Property of methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate

There total 6 articles about methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate 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: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-methyl 3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-((tertbutoxycarbonyl)amino)propanoate → methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate (1607804-26-1)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 30h; Inert atmosphere;

DOI:10.1002/ejoc.201801608

Reference yield:

levodopa (59-92-7,90638-38-3) → methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate (1607804-26-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride / 16 h / 0 °C / Inert atmosphere; Reflux

2.1: sodium hydrogencarbonate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

3.2: 15 h / 0 - 40 °C / Inert atmosphere; Sealed tube

4.1: iodine; potassium carbonate / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

4.2: 2.5 h / 20 °C / Inert atmosphere

5.1: triethylamine; dmap / acetonitrile / 30 h / 20 °C / Inert atmosphere

With dmap; thionyl chloride; iodine; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.201801608

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl (S)-3-(4,5-bis(ethoxymethoxy)-2-iodophenyl)-2-(di-(tert-butoxycarbonyl)amino)propanoate (1607804-26-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydrogencarbonate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

2.2: 15 h / 0 - 40 °C / Inert atmosphere; Sealed tube

3.1: iodine; potassium carbonate / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

3.2: 2.5 h / 20 °C / Inert atmosphere

4.1: triethylamine; dmap / acetonitrile / 30 h / 20 °C / Inert atmosphere

With dmap; iodine; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.201801608

upstream raw materials:

di-tert-butyl dicarbonate

levodopa

L-DOPA methyl ester

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate

Downstream raw materials:

2-(diacetoxyiodo)-1-[(2S)-2-[(di-tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl]-4,5-bis(ethoxymethoxy)benzene

Refernces