Boc-4-(trifluoromethyl)-D-phenylalanine

Base Information

• Chemical Name: Boc-4-(trifluoromethyl)-D-phenylalanine
• CAS No.: 82317-83-7
• Molecular Formula: C15H18F3NO4
• Molecular Weight: 333.307
• Hs Code.: 2924297099
• Mol file: 82317-83-7.mol

Synonyms:82317-83-7;Boc-4-(trifluoromethyl)-D-phenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid;Boc-4-Trifluoromethyl-D-Phenylalanine;Boc-D-Phe(4-CF3)-OH;Boc-D-4-Trifluoromethylphenylalanine;D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(trifluoromethyl)-;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(trifluoromethyl)phenyl]propanoic acid;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-(TRIFLUOROMETHYL)PHENYL)PROPANOIC ACID;MFCD00792407;(2R)-2-[(tert-butoxycarbonyl)amino]-3-[4-(trifluoromethyl)phenyl]propanoic acid;Boc-L-phe(4-CF3)-OH;SCHEMBL3556235;AKOS015890209;AC-9981;AM83502;CS-W009849;GS-6171;H10503;Boc-D-Phe(4-CF3)-OH, >=98.0% (TLC);N-(t-butoxycarbonyl)-4-(trifluoromethyl)-d-phenylalanine;N-(tert-butoxycarbonyl)-4-(trifluoromethyl)-D-phenylalanine;N-[(1,1-dimethylethoxy)carbonyl]-4-(trifluoromethyl)-D-phenylalanine;(R)-2-(tert-butoxycarbonylamino)-3-(4-(trifluoromethyl)phenyl) propanoic acid;4-(Trifluoromethyl)-L-phenylalanine, N-BOC protected (Boc-L-Phe(4-CF3)-OH)

Chemical Property of Boc-4-(trifluoromethyl)-D-phenylalanine

Chemical Property:

• Melting Point: 135-140 °C
• Boiling Point: 431.4 °C at 760 mmHg
• PKA: 3.76±0.10(Predicted)
• Flash Point: 214.7 °C
• PSA: 75.63000
• Density: 1.271 g/cm³
• LogP: 3.61670
• Storage Temp.: Keep Cold
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 333.11879254
• Heavy Atom Count: 23
• Complexity: 423

Purity/Quality:

97% ^*data from raw suppliers

Boc-p-trifluoromethyl-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)C(F)(F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=C(C=C1)C(F)(F)F)C(=O)O

Technology Process of Boc-4-(trifluoromethyl)-D-phenylalanine

There total 10 articles about Boc-4-(trifluoromethyl)-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: 89.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + (S)-4-trifluoromethylphenylalanine (3832-75-5,14091-16-8,114872-99-0,114926-38-4) → N-tert-butoxycarbonyl-L-4-trifluoromethylphenylalanine (82317-83-7,114873-07-3)

Guidance literature:

DOI:10.1248/cpb.37.826

Reference yield: 84.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-Amino-3-(4-trifluoromethyl-phenyl)-propionic acid; hydrochloride (3832-77-7,82337-63-1,122839-50-3,122839-56-9) → (R)-2-((tert-butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoic acid (82317-83-7)

Guidance literature:

With sodium hydroxide; magnesium oxide; In 1,4-dioxane; at 25 ℃;

DOI:10.1021/jm00349a006

Reference yield: 60.0%

4-bromomethyltrifluoromethylbenzene (402-49-3) → N-tert-butoxycarbonyl-L-4-trifluoromethylphenylalanine (82317-83-7,114873-07-3)

Guidance literature:

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-Amino-3-(4-trifluoromethyl-phenyl)-propionic acid; hydrochloride

2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid

diethyl 2-acetamido-2-<<4-(trifluoromethyl)phenyl>methyl>malonate

Downstream raw materials:

tert-butyl (S)-(1-(benzyl(methyl)amino)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-yl)carbamate

(2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(4-trifluoromethyl-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

C₂₇H₄₀F₃N₃O₆S

C₂₃H₃₂F₃N₃O₅S

Refernces

• 1、 Blake, James F.,Kallan, Nicholas C.,Xiao, Dengming,Xu, Rui,Bencsik, Josef R.,Skelton, Nicholas J.,Spencer, Keith L.,Mitchell, Ian S.,Woessner, Richard D.,Gloor, Susan L.,Risom, Tyler,Gross, Stefan D.,Martinson, Matthew,Morales, Tony H.,Vigers, Guy P.A.,Brandhuber, Barbara J.. "Discovery of pyrrolopyrimidine inhibitors of Akt". scheme or table. p. 5607 - 5612. Retrieved 2010/11/17.
• 2、 Hagiwara, Daijiro,Miyake, Hiroshi,Igari, Norihiro,Karino, Masako,Maeda, Yasue,et al.. "Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds". . p. 2090 - 2099. Retrieved 2007/10/02.