N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine Methyl Ester

Base Information

• Chemical Name: N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine Methyl Ester
• CAS No.: 853759-49-6
• Molecular Formula: C17H24FNO6
• Molecular Weight: 357.379
• Mol file: 853759-49-6.mol

Synonyms:N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine Methyl Ester;N-[(1,1-DiMethylethoxy)carbonyl]-2-fluoro-5-Methoxy-O-Methyl-L-tyrosine Methyl Ester;N-Butoxycarbonyl-4,5-diMethoxy-2-fluoro-L-phenylalanine Methyl Ester

Chemical Property of N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine Methyl Ester

Chemical Property:

• Boiling Point: 462.1±45.0 °C(Predicted)
• PKA: 10.81±0.46(Predicted)
• PSA: 86.58000
• Density: 1.167±0.06 g/cm3(Predicted)
• LogP: 2.65610
• Solubility.: Dichloromethane,

Purity/Quality:

97% ^*data from raw suppliers

N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine Methyl Ester

There total 7 articles about N-tert-Butoxycarbonyl-2-fluoro-5-methoxy-4-O-methyl-L-tyrosine 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: 93.0%

methyl-2-[(tert-butoxycarbonyl)amino]-3-(2-fluoro-4,5-dimethoxyphenyl)prop-2-enoate (853759-47-4) → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine methyl ester (853759-49-6)

Guidance literature:

With hydrogen; (+)-1,2-bis((2S,5S)-2,5-diethylphosphorano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In methanol; ethyl acetate; under 1551.49 Torr;

Reference yield:

C17H24AgNO6 (1421282-68-9) → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine methyl ester (853759-49-6)

Guidance literature:

With Selectfluor; In acetone; at 20 ℃; for 0.5h; Molecular sieve;

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-fluoro-L-phenylalanine methyl ester (853759-49-6)

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: Selectfluor / acetone / 0.5 h / 20 °C / Molecular sieve

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; Selectfluor; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetone;

DOI:10.1039/c2cc38646a

upstream raw materials:

methyl-2-[(tert-butoxycarbonyl)amino]-3-(2-fluoro-4,5-dimethoxyphenyl)prop-2-enoate

(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

Downstream raw materials:

3,4-dihydroxy-6-fluoro-L-phenylalanine

Refernces

• 1、 -. "Method for making fluorine labled L-Dopa". Page/Page column 5. . Retrieved 2008/06/13.