(R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

Base Information

• Chemical Name: (R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester
• CAS No.: 331731-27-2
• Molecular Formula: C₁₃H₁₂Cl₃FN₂O₆
• Molecular Weight: 417.605

Synonyms:(R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

Chemical Property of (R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

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Technology Process of (R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

There total 3 articles about (R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine 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%

D-(4-fluoro-3-nitrophenyl)glycine methyl ester (169825-21-2) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → (R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-27-2)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 25 ℃; for 15h;

DOI:10.1021/ja003835i

Reference yield:

4-(bromomethyl)-1-fluoro-2-nitrobenzene (15017-52-4) → (R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / n-BuLi; CuCN

2: 87 percent / TFA

3: 93 percent / NaHCO₃ / CH₂Cl₂ / 15 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-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / TFA

2: 93 percent / NaHCO₃ / CH₂Cl₂ / 15 h / 25 °C

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja003835i

upstream raw materials:

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

2,2,2-Trichloroethyl chloroformate

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:

(S)-{3-[5-((R)-2-Benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[(R)-3-(4-fluoro-3-nitro-phenyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionylamino]-acetic acid

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

(R)-N-trichloroethoxycarbonyl-4-fluoro-3-nitrophenylalanine

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