(S)-3-fluoro-4-nitrophenylalanine methyl ester

Base Information

• Chemical Name: (S)-3-fluoro-4-nitrophenylalanine methyl ester
• CAS No.: 160247-85-8
• Molecular Formula: C₁₀H₁₁FN₂O₄
• Molecular Weight: 242.207
• Mol file: 160247-85-8.mol

Synonyms:(S)-3-fluoro-4-nitrophenylalanine methyl ester

Chemical Property of (S)-3-fluoro-4-nitrophenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-fluoro-4-nitrophenylalanine methyl ester

There total 9 articles about (S)-3-fluoro-4-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: 92.0%

(2S,5R)-2-(3'-fluoro-4'-nitrobenzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (160247-84-7) → L-Valine methyl ester (4070-48-8) + (S)-3-fluoro-4-nitrophenylalanine methyl ester (160247-85-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1021/jo951375j

Reference yield: 91.0%

(2S,5R)-2-(3'-fluoro-4'-nitrobenzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (160247-84-7) → (S)-3-fluoro-4-nitrophenylalanine methyl ester (160247-85-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; acetonitrile; Ambient temperature;

DOI:10.1016/0040-4039(94)85322-3

Reference yield:

4-(bromomethyl)-2-fluoro-1-nitrobenzene (131858-37-2) → (S)-3-fluoro-4-nitrophenylalanine methyl ester (160247-85-8)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH / dimethylformamide / 4 h / Ambient temperature

2: conc. aq. HCl / 20 h / Heating

3: SOCl₂ / 5 h / 40 °C

4: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

5: phosphate buffer, protease rype VIII-A from Bacillus lichenifor / CH₂Cl₂ / 6 h / 37 °C

6: 1.) SOCl₂, 2.) aq. K₂CO₃ / 15 h / Heating

With hydrogenchloride; thionyl chloride; phosphate buffer; protease rype VIII-A from Bacillus lichenifor; sodium hydride; potassium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(96)00524-1

upstream raw materials:

(2S,5R)-2-(3'-fluoro-4'-nitrobenzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

methanol

(S)-N-trifluoroacetyl-3-fluoro-4-nitrophenylalanine

(R,S)-3-fluoro-4-nitrophenylalanine hydrochloride

Downstream raw materials:

(S)-2-[(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-methoxy-phenyl)-propionylamino]-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester

3-fluoro-4-nitro-N--L-phenylalanine methyl ester

3-fluoro-4-nitro-N-[N-(tert-butyloxycarbonyl)-N-methyl-D-tyrosyl]-L-phenylalanine methyl ester

3-fluoro-4-nitro-N-[N-(tert-butyloxycarbonyl)-N-methyl-L-tyrosyl]-L-phenylalanine methyl ester

Refernces

• 1、 Vergne, Caroline,Bois-Choussy, Michele,Ouazzani, Jamal,Beugelmans, Rene,,Zhu, Jieping. "Chemoenzymatic synthesis of enantiomerically pure 4-fluoro-3-nitro and 3-fluoro-4-nitro phenylallanine". . p. 391 - 398. Retrieved 2007/10/03.
• 2、 Beugelmans, Rene,Bigot, Antony,Bois-Choussy, Michele,Zhu, Jieping. "A new approach to the synthesis of piperazinomycin and bouvardin: Facile access to cycloisodityrosine via an intramolecular SNAr reaction". . p. 771 - 774. Retrieved 2007/10/03.