Z-P-FLUORO-PHE-OH

Base Information

• Chemical Name: Z-P-FLUORO-PHE-OH
• CAS No.: 17543-58-7
• Molecular Formula: C17H16FNO4
• Molecular Weight: 317.317
• Hs Code.: 2924299090
• Mol file: 17543-58-7.mol

Synonyms:Alanine,N-carboxy-3-(p-fluorophenyl)-, N-benzyl ester, L- (8CI);N-Carbobenzoxy-p-fluoro-L-phenylalanine;Z-Phe(4-F)-OH;

Chemical Property of Z-P-FLUORO-PHE-OH

Chemical Property:

• Melting Point: 158-160℃ (ethyl acetate ligroine )
• Boiling Point: 515.754 °C at 760 mmHg
• Flash Point: 265.718 °C
• PSA: 75.63000
• Density: 1.301 g/cm³
• LogP: 3.13870
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Z-4-fluoro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-P-FLUORO-PHE-OH

There total 14 articles about Z-P-FLUORO-PHE-OH 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: 95.0%

L-4-fluorophenylalanine (1132-68-9) + benzyl chloroformate (501-53-1,94274-21-2) → 2S-2-benzyloxycarbonylamino-2-(4-fluorophenylmethyl)-acetic acid (17543-58-7)

Guidance literature:

With sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; water; at 20 ℃;

Reference yield:

4-(4-fluoro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester (394210-36-7) → (R)-(N-benzyloxycarbonyl)-p-fluorophenylalanine (117467-73-9) + 2S-2-benzyloxycarbonylamino-2-(4-fluorophenylmethyl)-acetic acid (17543-58-7)

Guidance literature:

4-(4-fluoro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester; With methanol; 4 A molecular sieve; In diethyl ether; at -78 ℃; for 31h;

With water; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja011936q

Reference yield:

4-Fluorophenylalanine (51-65-0) → 2S-2-benzyloxycarbonylamino-2-(4-fluorophenylmethyl)-acetic acid (17543-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 50 °C

2.1: NMM / tetrahydrofuran / -25 - 20 °C

3.1: 10 mol percent (DHQD)2AQN; 4 Angstroem molecular sieves; methanol / diethyl ether / 31 h / -78 °C

3.2: H₂O

With 4-methyl-morpholine; methanol; 4 A molecular sieve; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja011936q

upstream raw materials:

Z-DL-Phe(4F)-OCH₂CF₃

ethyl N-benzyloxycarbonyl-4-fluorophenylalaninate

L-4-fluorophenylalanine

benzyl chloroformate

Downstream raw materials:

L-4-fluorophenylalanine

methyl 2-[(2S)-1-[(2S)-2-[(benzyloxycarbonyl)amino]-3-(4-fluorophenyl)propanoyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxopiperazinyl]acetate

C₂₁H₂₅FN₂O₅

C₃₉H₄₀FN₅O₂

Refernces

• 1、 Danalev, Dancho,Borisova, Desislava,Yaneva, Spaska,Georgieva, Maya,Balacheva, Anelia,Dzimbova, Tatyana,Iliev, Ivan,Pajpanova, Tamara,Zaharieva, Zdravka,Givechev, Ivan,Naydenova, Emilia. "Synthesis, in vitro biological activity, hydrolytic stability and docking of new analogs of BIM-23052 containing halogenated amino acids". . p. 1581 - 1592. Retrieved 2020/11/23.
• 2、 Miyazawa, Toshifumi,Nakajo, Shin'ichi,Nishikawa, Miyako,Hamahara, Kazumi,Imagawa, Kiwamu,Ensatsu, Eiichi,Yanagihara, Ryoji,Yamada, Takashi. "α-chymotrypsin-catalysed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in organic solvents with low water content: Incorporation of non-protein amino acids into peptides". . p. 82 - 86. Retrieved 2007/10/03.