(5-fluoro)DOPA

Base Information

• Chemical Name: (5-fluoro)DOPA
• CAS No.: 1227828-13-8
• Molecular Formula: C₂₅H₃₆FNO₁₀
• Molecular Weight: 529.56
• Mol file: 1227828-13-8.mol

Synonyms:(5-fluoro)DOPA

Chemical Property of (5-fluoro)DOPA

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5-fluoro)DOPA

There total 4 articles about (5-fluoro)DOPA 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: 70.0%

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-trimethylstannyl-L-phenylalaninemethyl ester (857502-21-7) → (5-fluoro)DOPA (1227828-13-8)

Guidance literature:

With sodium triflate; sodium hydrogencarbonate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate); silver(l) oxide; In acetone; at 23 - 65 ℃;

Reference yield:

(S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester (211619-93-1) → (5-fluoro)DOPA (1227828-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / toluene / 9 h / 80 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / 1,4-dioxane / 5 h / 100 °C

3: Selectfluor; sodium hydrogencarbonate; sodium triflate; silver(l) oxide / acetone / 5 h / 65 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium triflate; sodium hydrogencarbonate; Selectfluor; triethylamine; lithium chloride; silver(l) oxide; In 1,4-dioxane; acetone; toluene;

DOI:10.1021/ja3084797

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (5-fluoro)DOPA (1227828-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / toluene / 9 h / 80 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / 1,4-dioxane / 5 h / 100 °C

3: Selectfluor; sodium hydrogencarbonate; sodium triflate; silver(l) oxide / acetone / 5 h / 65 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium triflate; sodium hydrogencarbonate; Selectfluor; triethylamine; lithium chloride; silver(l) oxide; In 1,4-dioxane; acetone; toluene;

DOI:10.1021/ja3084797

upstream raw materials:

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-trimethylstannyl-L-phenylalaninemethyl ester

di-tert-butyl dicarbonate

(S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester

N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-bromo-L-phenylalaninemethyl ester