Boc-3,4-difluoro-D-phenylalanine

Base Information

• Chemical Name: Boc-3,4-difluoro-D-phenylalanine
• CAS No.: 205445-51-8
• Molecular Formula: C₁₄H₁₇F₂NO₄
• Molecular Weight: 301.29
• Hs Code.: 2924297099
• European Community (EC) Number: 606-577-0
• DSSTox Substance ID: DTXSID50371196
• Wikidata: Q72449136
• Mol file: 205445-51-8.mol

Synonyms:205445-51-8;Boc-3,4-difluoro-D-phenylalanine;BOC-d-3,4-Difluorophenylalanine;boc-d-phe(3,4-dif)-oh;N-(tert-Butoxycarbonyl)-3,4-difluoro-D-phenylalanine;(2R)-3-(3,4-difluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(R)-2-((tert-butoxycarbonyl)amino)-3-(3,4-difluorophenyl)propanoic acid;Boc-D-Phe(3,4-F2)-OH;Boc-D-Phe(3,4-F)-OH;SCHEMBL2573377;DTXSID50371196;CYAOPVHXASZUDE-LLVKDONJSA-N;D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3,4-difluoro-;MFCD00672519;N-Boc-3,4-difluoro-D-phenylalanine;AKOS015889850;AC-9061;AM82098;CS-W014540;HY-W013824;AS-15595;B3626;A50126;A814667;Boc-D-Phe(3,4-F2)-OH, >=98.0% (TLC);J-300395;N-tert-Butoxycarbonyl-D-3,4-Difluoro Phenylalanine;2-(tert-butoxycarbonylamino)-3-(3,4-difluorophenyl)propanoic acid;(r)-2-(tert-butoxycarbonylamino)-3-(3,4-difluorophenyl)propanoic acid;N-alpha-t-Butyloxycarbonyl-D-3,4-difluorophenylalanine (Boc-D-Phe(3,4-F2)-OH)

Chemical Property of Boc-3,4-difluoro-D-phenylalanine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 98-110 °C
• Boiling Point: 430.4 °C at 760 mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: 214.1 °C
• PSA: 75.63000
• Density: 1.27 g/cm³
• LogP: 2.87610
• Storage Temp.: Store at 0°C
• Solubility.: soluble in Methanol
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 301.11256435
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-3,4-difluoro-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)F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC(=C(C=C1)F)F)C(=O)O
• Uses: Boc-D-3,4-Difluorophenylalanine is used in the discovery of pyrrolopyrimidine inhibitors of Akt as antitumor agents.

Technology Process of Boc-3,4-difluoro-D-phenylalanine

There total 6 articles about Boc-3,4-difluoro-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: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + (L)-2-amino-3-(3,4-difluorophenyl)propanoic acid (31105-90-5,249648-08-6) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4-difluorophenyl)propanoic acid (198474-90-7,1214041-87-8,205445-51-8)

Guidance literature:

DOI:10.1016/S0040-4039(99)02191-7

Reference yield:

C15H19F2NO4 (176795-00-9) → N-(tert-butoxycarbonyl)-3,4-difluoro-D-phenylalanine (1214041-87-8,205445-51-8)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 6h;

DOI:10.1016/j.bmcl.2010.08.053

Reference yield:

2-Acetylamino-2-(3,4-difluorobenzyl)malonic acid diethyl ester (15017-45-5) → (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4-difluorophenyl)propanoic acid (198474-90-7,1214041-87-8,205445-51-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2M NaOH / methanol; H₂O / 3 h / 40 °C

2: 92 percent / p-xylene / 2 h / Heating

3: Aspergillus genus acylase; 0.2 M AcONa; 0.2 M NaOH / H₂O / 48 h / 38 °C / pH 8.0

4: 94 percent

With sodium hydroxide; Aspergillus genus acylase; sodium acetate; In methanol; para-xylene; water; 1: Hydrolysis / 2: Decarboxylation / 3: Deacetylation / 4: Acylation;

DOI:10.1016/S0040-4039(99)02191-7

upstream raw materials:

di-tert-butyl dicarbonate

(L)-2-amino-3-(3,4-difluorophenyl)propanoic acid

2-Acetylamino-2-(3,4-difluorobenzyl)malonic acid diethyl ester

alpha-bromo-3,4-difluorotoluene

Downstream raw materials:

tert-butyl [(2R)-3-(3,4-difluorophenyl)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl]piperidin-1-yl}-1-oxopropan-2-yl]carbamate

(4aS,8aR)-2-{1-[(2R)-2-amino-3-(3,4-difluorophenyl)propanoyl]piperidin-4-yl}-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one hydrochloride

C₂₁H₂₂BrF₂N₃O₄

C₂₄H₂₃F₂N₅O₃

Refernces

• 1、 Fujita, Tsugumi,Nose, Takeru,Matsushima, Ayami,Okada, Kazushi,Asai, Daisuke,Yamauchi, Yasuko,Shirasu, Naoto,Honda, Takeshi,Shigehiro, Daiki,Shimohigashi, Yasuyuki. "Synthesis of a complete set of L-difluorophenylalanines, L-(F2)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor". . p. 923 - 927. Retrieved 2007/10/03.