Fmoc-Phe(4-CF3)-OH

Base Information

• Chemical Name: Fmoc-Phe(4-CF3)-OH
• CAS No.: 247113-86-6
• Molecular Formula: C₂₅H₂₀F₃NO₄
• Molecular Weight: 455.433
• Hs Code.: 2924299090
• European Community (EC) Number: 694-926-8,695-782-9
• DSSTox Substance ID: DTXSID10427325
• Wikidata: Q72479003
• Mol file: 247113-86-6.mol

Synonyms:247113-86-6;Fmoc-Phe(4-CF3)-OH;Fmoc-4-(trifluoromethyl)-L-phenylalanine;Fmoc-L-4-Trifluoromethylphenylalanine;Fmoc-4-Trifluoromethyl-L-Phenylalanine;FMOC-L-4-TRIFLUOROMETHYLPHE;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(trifluoromethyl)phenyl]propanoic acid;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid;238742-88-6;(2S)-2-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-3-[4-(trifluoromethyl)phenyl]propanoic acid;N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-(trifluoromethyl)-D-phenylalanine;SCHEMBL3724885;DTXSID10427325;YMEGJWTUWMVZPD-QFIPXVFZSA-N;L-Fmoc-4-trifluoromethylphenylalanine;MFCD00797581;AKOS015837278;L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-(trifluoromethyl)-;AC-9984;AM83503;CS-W009648;GS-6057;(2S)-2-[[9H-fluoren-9-ylmethoxy(oxo)methyl]amino]-3-[4-(trifluoromethyl)phenyl]propanoic acid;AC-16854;N-Fmoc-4-(trifluoromethyl)-L-phenylalanine;Fmoc-Phe(4-CF3)-OH, >=97% (HPLC);H10505;EN300-3405427;A817453;J-015636;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-4-(trifluoromethyl)-L-phenylalanine;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(4-(TRIFLUOROMETHYL)PHENYL)PROPANOIC ACID

Chemical Property of Fmoc-Phe(4-CF3)-OH

Chemical Property:

• Melting Point: 128-138 °C
• Boiling Point: 619 °C at 760 mmHg
• PKA: 3.65±0.10(Predicted)
• Flash Point: 328.2 °C
• PSA: 75.63000
• Density: 1.351 g/cm³
• LogP: 5.63070
• Storage Temp.: 2-8°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 455.13444261
• Heavy Atom Count: 33
• Complexity: 670

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-p-trifluoromethyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)C(F)(F)F)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)C(F)(F)F)C(=O)O

Technology Process of Fmoc-Phe(4-CF3)-OH

There total 10 articles about Fmoc-Phe(4-CF3)-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:

C26H22F3NO4 → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid (247113-86-6)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/ja512690x

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-(trifluoromethyl)phenylalanine hydrochloride → C25H20F3NO4 (247113-86-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.7b00523

Reference yield:

1-Fluoro-3-iodobenzene (1121-86-4) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid (247113-86-6)

Guidance literature:

Multi-step reaction with 5 steps

1: α-picoline; palladium diacetate; silver(I) acetate / 24 h / 20 - 75 °C / Sealed tube

2: [bis(acetoxy)iodo]benzene / 3 h / 80 °C

3: ethylenediamine / dichloromethane; methanol / 10 h / 20 - 40 °C

4: sodium hydrogencarbonate / water; 1,4-dioxane / 0 - 20 °C

5: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / 0 °C

With α-picoline; lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; silver(I) acetate; palladium diacetate; sodium hydrogencarbonate; ethylenediamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/ja512690x

upstream raw materials:

1-Fluoro-3-iodobenzene

4-methylbenzotrifluoride

(fluorenylmethoxy)carbonyl chloride

4-bromomethyltrifluoromethylbenzene

Downstream raw materials:

O-W-F-F(4-CF₃)-F-H(1-Bzl)-NH₂

O-W-F(4-CF₃)-I-F-H(1-Bzl)-NH₂

O-W-F-I-F(4-CF₃)-H(1-Bzl)-NH₂

Refernces

• 1、 Chen, Gang,Shigenari, Toshihiko,Jain, Pankaj,Zhang, Zhipeng,Jin, Zhong,He, Jian,Li, Suhua,Mapelli, Claudio,Miller, Michael M.,Poss, Michael A.,Scola, Paul M.,Yeung, Kap-Sun,Yu, Jin-Quan. "Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary". . p. 3338 - 3351. Retrieved 2015/03/30.