Boc-3,5-difluoro-L-phenylalanine

Base Information

• Chemical Name: Boc-3,5-difluoro-L-phenylalanine
• CAS No.: 205445-52-9
• Molecular Formula: C14H17F2NO4
• Molecular Weight: 301.29
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40942718
• Wikidata: Q72449127
• Mol file: 205445-52-9.mol

Synonyms:205445-52-9;Boc-L-3,5-Difluorophenylalanine;BOC-3,5-DIFLUORO-L-PHENYLALANINE;BOC-PHE(3,5-F2)-OH;(S)-N-Boc-3,5-difluorophenylalanine;N-BOC-3,5-DIFLUORO-L-PHENYLALANINE;BOC-PHE(3,5-DIF)-OH;BOC-L-3,5-DIFLUOROPHE;N-BOC-L-3,5-DIFLUOROPHENYLALANINE;(2S)-3-(3,5-difluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-3-(3,5-difluorophenyl)propanoic acid;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propionic acid;N-(tert-butoxycarbonyl)-3,5-difluoro-L-phenylalanine;SCHEMBL1448035;DTXSID40942718;CZBNUDVCRKSYDG-NSHDSACASA-N;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3,5-difluoro-;MFCD00797556;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid;AKOS015889851;AC-9065;HY-W037441;PS-11016;A4465;CS-0093741;3,5-Difluoro-L-phenylalanine,N-BOC protected;N10805;EN300-3345894;AS-813/43497447;N-(tert-butoxycarbonyl)-3,5-difluorophenylalanine;Boc-Phe(3,5-F2)-OH, >=98.0% (HPLC);J-013398;3,5-DIFLUORO-L-PHENYLALANINE, N-BOC PROTECTED;2,4-BIS(ACETYLAMINOMETHYL)-1,5-DIMETHYLBENZENE;(S)-2-(Boc-amino)-3-(3,5-difluorophenyl)propionic acid;N-[tert-Butoxy(hydroxy)methylidene]-3,5-difluorophenylalanine;2-(S)-tert-butoxycarbonylamino-3-(3,5-difluorophenyl)propionic acid;3,5-Difluoro-D-phenylalanine, N-BOC protected (Boc-D-Phe(3,5-diF)-OH);(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3,5-difluorophenyl)propanoic acid;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(3,5-DIFLUOROPHENYL)PROPANOIC ACID

Chemical Property of Boc-3,5-difluoro-L-phenylalanine

Chemical Property:

• Vapor Pressure: 1.01E-07mmHg at 25°C
• Melting Point: 115℃
• Refractive Index: 1.506
• Boiling Point: 417.6 °C at 760mmHg
• PKA: 3.73±0.10(Predicted)
• Flash Point: 206.4 °C
• PSA: 75.63000
• Density: 1.27 g/cm³
• LogP: 2.87610
• Storage Temp.: Store at 0°C
• 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: 374

Purity/Quality:

99% ^*data from raw suppliers

Boc-3,5-difluoro-L-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(=CC(=C1)F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC(=C1)F)F)C(=O)O
• Uses: Used as pharmaceutical intermediates.

Technology Process of Boc-3,5-difluoro-L-phenylalanine

There total 5 articles about Boc-3,5-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) + (S)-2-amino-3-(3,5-difluorophenyl)propanoic acid (31105-91-6,266360-63-8) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid (205445-52-9,669057-06-1)

Guidance literature:

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

Reference yield:

1-bromomethyl-3,5-difluoro-benzene (141776-91-2) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid (205445-52-9,669057-06-1)

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

Reference yield:

2-acetylamino-3-(3,5-difluoro-phenyl)-propionic acid (266360-52-5) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid (205445-52-9,669057-06-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 94 percent

With sodium hydroxide; Aspergillus genus acylase; sodium acetate; In water; 1: Deacetylation / 2: Acylation;

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

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-amino-3-(3,5-difluorophenyl)propanoic acid

1-bromomethyl-3,5-difluoro-benzene

2-acetylamino-3-(3,5-difluoro-phenyl)-propionic acid

Downstream raw materials:

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3,5-difluorophenyl)propanoate

(S)-[1-(3,5-difluorobenzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

(S)-[1-(3,5-difluorobenzyl)-prop-2-ynyl]-carbamic acid tert-butyl ester

(S)-[3,3-dibromo-1-(3,5-difluorobenzyl)allyl]carbamic acid tert-butyl ester