Boc-3,4-difluoro-L-phenylalanine

Base Information

• Chemical Name: Boc-3,4-difluoro-L-phenylalanine
• CAS No.: 198474-90-7
• Molecular Formula: C14H17F2NO4
• Molecular Weight: 301.29
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID00427298
• Wikidata: Q72449133
• Mol file: 198474-90-7.mol

Synonyms:198474-90-7;Boc-L-3,4-Difluorophenylalanine;Boc-3,4-difluoro-L-phenylalanine;boc-phe(3,4-dif)-oh;Boc-Phe(3,4-F2)-OH;(2S)-3-(3,4-difluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-BOC-3,4-DIFLUORO-L-PHENYLALANINE;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(3,4-difluorophenyl)propionic acid;MFCD00672518;Boc-3,4-difluoro-Phe-OH;Boc-Phe(3,4-F)-OH;Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3,4-difluoro-;N-(tert-Butoxycarbonyl)-3,4-difluoro-L-phenylalanine;SCHEMBL1516520;DTXSID00427298;CYAOPVHXASZUDE-NSHDSACASA-N;CS-M2915;(s)-2-(tert-butoxycarbonylamino)-3-(3,4-difluorophenyl)propanoic acid;(S)-2-((tert-butoxycarbonyl)amino)-3-(3,4-difluorophenyl)propanoic acid;AKOS016842519;AC-9062;AM82097;AC-22419;AS-15598;HY-79165;PD196108;B3627;A814000;Boc-Phe(3,4-F2)-OH, >=98.0% (TLC);J-300394;N-tert-Butoxycarbonyl-L-3,4-Difluoro Phenylalanine;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3,4-difluoro-;(S)-2-(tert-butoxycarbonylamino)-3-(3,4-difluorophenyl)propanoicacid;(2S)-2-(tert-butoxycarbonylamino)-3-(3,4-difluorophenyl)propanoic acid;Boc-3,4-Difluoro-L-phenylalanine

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

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.57E-08mmHg at 25°C
• Melting Point: 95-105 °C
• Refractive Index: 1.506
• 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.: slightly sol. 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% ^*data from raw suppliers

Boc-L-3,4-difluorophenylalanine ^*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

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

There total 5 articles about Boc-3,4-difluoro-L-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:

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

Reference yield:

alpha-bromo-3,4-difluorotoluene (85118-01-0) → (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 5 steps

1: 90 percent / NaOEt / ethanol / 2 h / Heating

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

3: 92 percent / p-xylene / 2 h / Heating

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

5: 94 percent

With sodium hydroxide; Aspergillus genus acylase; sodium ethanolate; sodium acetate; In methanol; ethanol; para-xylene; water; 1: Alkylation / 2: Hydrolysis / 3: Decarboxylation / 4: Deacetylation / 5: 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:

3-methyl-1H-pyrrole-2-carboxylic acid [(S)-1-[(6-amino-pyridin-3-ylmethyl)-carbamoyl]-2-(3,4-difluoro-phenyl)-ethyl]-amide trifluoroacetate

(R)-1-methyl-pyrrolidine-2-carboxylic acid [(S)-1-[(6-amino-pyridin-3-ylmethyl)-carbamoyl]-2-(3,4-difluoro-phenyl)-ethyl]-amide

((S)-2-(3,4-difluoro-phenyl)-1-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-benzylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester

[(S)-1-[(2-amino-thiazol-5-ylmethyl)-carbamoyl]-2-(3,4-difluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester

Refernces