N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[¹⁸F]fluoro-L-phenylalanine methyl ester

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[¹⁸F]fluoro-L-phenylalanine methyl ester
• CAS No.: 1421282-70-3
• Molecular Formula: C₁₇H₂₄FNO₆
• Molecular Weight: 356.381
• Mol file: 1421282-70-3.mol

Synonyms:

Chemical Property of N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[¹⁸F]fluoro-L-phenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[¹⁸F]fluoro-L-phenylalanine methyl ester

There total 6 articles about N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[¹⁸F]fluoro-L-phenylalanine methyl 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:

C17H24AgNO6 (1421282-68-9) → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[18F]fluoro-L-phenylalanine methyl ester (1421282-70-3)

Guidance literature:

With ⁽¹⁸⁾F-1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane ditriflate; In [⁽²⁾H₆]acetone; at 20 ℃; for 0.333333h;

DOI:10.1039/c2cc38646a

Reference yield:

N-(tert-butoxycarbonyl)-3,4-(dimethoxy)-6-(iodo)-L-phenylalanine (1421282-26-9) → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[18F]fluoro-L-phenylalanine methyl ester (1421282-70-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane; methanol / 20 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 17.17 h / 80 °C / Inert atmosphere

3.1: sodium hydroxide / methanol / 3 h / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

4.1: ⁽¹⁸⁾F-1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane ditriflate / [⁽²⁾H₆]acetone / 0.33 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ⁽¹⁸⁾F-1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane ditriflate; potassium acetate; sodium hydroxide; In methanol; [⁽²⁾H₆]acetone; dichloromethane; dimethyl sulfoxide;

DOI:10.1039/c2cc38646a

Reference yield:

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-iodo-4,5-dimethoxyphenyl)propanoate (1421282-25-8) → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[18F]fluoro-L-phenylalanine methyl ester (1421282-70-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hydroxide / water; tetrahydrofuran / 2 h / 20 °C

2.1: dichloromethane; methanol / 20 °C

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 17.17 h / 80 °C / Inert atmosphere

4.1: sodium hydroxide / methanol / 3 h / Inert atmosphere

4.2: 0.5 h / 0 °C / Inert atmosphere

5.1: ⁽¹⁸⁾F-1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane ditriflate / [⁽²⁾H₆]acetone / 0.33 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ⁽¹⁸⁾F-1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane ditriflate; potassium acetate; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; [⁽²⁾H₆]acetone; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1039/c2cc38646a

upstream raw materials:

(S)-ethyl 2-(N-(tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate

N-(tert-butoxycarbonyl)-3,4-(dimethoxy)-6-(iodo)-L-phenylalanine

N-(tert-butoxycarbonyl)-3,4-(dimethoxy)-6-(iodo)-L-phenylalanine methyl ester

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-iodo-4,5-dimethoxyphenyl)propanoate

Downstream raw materials:

[18F]-L-3,4-dihydroxy-6-fluorophenylalanine