(R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester

Base Information

• Chemical Name: (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester
• CAS No.: 331731-29-4
• Molecular Formula: C₁₅H₁₆Cl₃FN₂O₆
• Molecular Weight: 445.659
• Mol file: 331731-29-4.mol

Synonyms:(R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester

Chemical Property of (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester

There total 3 articles about (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine 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: 82.0%

2,2,2-trichloro-1,1-dimethylethoxychloroformate (66270-36-8) + D-(4-fluoro-3-nitrophenyl)glycine methyl ester (169825-21-2) → (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester (331731-29-4)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1021/ja003835i

Reference yield:

4-(bromomethyl)-1-fluoro-2-nitrobenzene (15017-52-4) → (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester (331731-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / n-BuLi; CuCN

2: 87 percent / TFA

3: 82 percent / NaHCO₃ / CH₂Cl₂ / 3 h / 25 °C

With n-butyllithium; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; 1: Schollkopf alkylation;

DOI:10.1021/ja003835i

Reference yield:

(3R,6S)-2,5-dimethoxy-6-isopropyl-3-(4-fluoro-3-nitrophenyl)-3,6-dihydro-1,4-pyrazine (169825-20-1) → (R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine methyl ester (331731-29-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / TFA

2: 82 percent / NaHCO₃ / CH₂Cl₂ / 3 h / 25 °C

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja003835i

upstream raw materials:

2,2,2-trichloro-1,1-dimethylethoxychloroformate

D-(4-fluoro-3-nitrophenyl)glycine methyl ester

4-(bromomethyl)-1-fluoro-2-nitrobenzene

(3R,6S)-2,5-dimethoxy-6-isopropyl-3-(4-fluoro-3-nitrophenyl)-3,6-dihydro-1,4-pyrazine

Downstream raw materials:

[(R)-1-((S)-1-{3-[5-((R)-2-Benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-2-hydroxy-ethylcarbamoyl)-2-(4-fluoro-3-nitro-phenyl)-ethyl]-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester

(R)-N-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-4-fluoro-3-nitrophenyl-alanine