Boc-4-fluoro-D-phenylalanine

Base Information

• Chemical Name: Boc-4-fluoro-D-phenylalanine
• CAS No.: 57292-45-2
• Molecular Formula: C₁₄H₁₈FNO₄
• Molecular Weight: 283.3
• Hs Code.: 29242990
• European Community (EC) Number: 671-835-1
• DSSTox Substance ID: DTXSID80370334
• Nikkaji Number: J1.248.627H
• Mol file: 57292-45-2.mol

Synonyms:57292-45-2;Boc-D-Phe(4-F)-OH;BOC-d-4-Fluorophenylalanine;BOC-D-4-Fluorophe;Boc-4-fluoro-D-phenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoic acid;N-(tert-Butoxycarbonyl)-4-fluoro-D-phenylalanine;(2R)-3-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-;MFCD00079669;boc-4-fluoro-d-phe;boc-4-fluoro-l-phe;boc-p-fluoro-d-phe-oh;(2r)-2-[(tert-butoxycarbonyl)amino]-3-(4-fluorophenyl)propanoic acid;(2R)-2-{[(Tert-Butoxy)Carbonyl]Amino}-3-(4-Fluorophenyl)Propanoic Acid;N-TERT-BUTOXY-D-4-FLUORO PHENYLALANINE;SCHEMBL2109180;N-Boc-4-fluoro-D-phenylalanine;DTXSID80370334;RCXSXRAUMLKRRL-LLVKDONJSA-N;N-BOC-D-4-FLUOROPHENYLALANINE;AKOS016843602;Boc-3-(4-fluorophenyl)-(R)-alanine;AC-9900;AM83346;CS-W010038;HY-W009322;DS-15173;B3303;N10782;Boc-D-Phe(4-F)-OH, >=99.0% (TLC);EN300-1071444;A831375;J-300405;(r)-2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)propanoic acid;(r)-2-tert-butoxycarbonylamino-3-(4-fluoro-phenyl)-propionic acid;(R)-3-(4-Fluorophenyl)-2-(tert-butoxycarbonylamino)propionic acid;2-(R)-tert-butoxycarbonylamino-3-(4-fluorophenyl)propionic acid;N-alpha-t-Butyloxycarbonyl-D-4-fluorophenylalanine (Boc-D-Phe(4-F)-OH);(2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(4-fluorophenyl)propanoic acid;(2R)-2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)propanoate

Chemical Property of Boc-4-fluoro-D-phenylalanine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.36E-08mmHg at 25°C
• Melting Point: 83-86°C
• Boiling Point: 431.2 °C at 760 mmHg
• PKA: 3.87±0.10(Predicted)
• Flash Point: 214.6 °C
• PSA: 75.63000
• Density: 1.1918 (estimate)
• LogP: 2.73700
• Storage Temp.: Keep Cold
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 283.12198622
• Heavy Atom Count: 20
• Complexity: 346

Purity/Quality:

98%min ^*data from raw suppliers

N-(tert-Butoxycarbonyl)-4-fluoro-D-phenylalanine >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=C(C=C1)F)C(=O)O
• Uses: Boc-D-4-Fluorophenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-4-fluoro-D-phenylalanine

There total 6 articles about Boc-4-fluoro-D-phenylalanine 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%

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoate → Boc-Phe(p-F) (41153-30-4,57292-45-2,79561-25-4,129101-25-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b00002

Reference yield: 79.0%

di-tert-butyl dicarbonate (24424-99-5) + L-4-fluorophenylalanine (1132-68-9) → Boc-Phe(p-F) (41153-30-4,57292-45-2,79561-25-4,129101-25-3)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1021/acs.jmedchem.9b01199

Reference yield: 79.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + L-4-fluorophenylalanine (1132-68-9) → Boc-Phe(p-F) (41153-30-4,57292-45-2,79561-25-4,129101-25-3)

Guidance literature:

DOI:10.1248/cpb.37.826

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

L-4-fluorophenylalanine

di-tert-butyl dicarbonate

4-Fluorophenylalanine

Downstream raw materials:

tert-butyl N-[(1S)-1-[(4-fluorophenyl)methyl]-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate

(S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-fluoro-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid; hydrochloride

(S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-(4-fluoro-phenyl)-propionylamino]-4-methyl-pentanoic acid; hydrochloride

Boc-Phe(4-F)-NMeBzl

Refernces

• 1、 Subbaiah, Murugaiah A.M.,Mandlekar, Sandhya,Desikan, Sridhar,Ramar, Thangeswaran,Subramani, Lakshumanan,Annadurai, Mathiazhagan,Desai, Salil D.,Sinha, Sarmistha,Jenkins, Susan M.,Krystal, Mark R.,Subramanian, Murali,Sridhar, Srikanth,Padmanabhan, Shweta,Bhutani, Priyadeep,Arla, Rambabu,Singh, Shashyendra,Sinha, Jaydeep,Thakur, Megha,Kadow, John F.,Meanwell, Nicholas A.. "Design, Synthesis, and Pharmacokinetic Evaluation of Phosphate and Amino Acid Ester Prodrugs for Improving the Oral Bioavailability of the HIV-1 Protease Inhibitor Atazanavir". . p. 3553 - 3574. Retrieved 2019/04/17.
• 2、 Maity, Sibaprasad,Nir, Sivan,Zada, Tal,Reches, Meital. "Self-assembly of a tripeptide into a functional coating that resists fouling". supporting information. p. 11154 - 11157. Retrieved 2014/11/08.