(S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoic acid
• CAS No.: 167993-07-9
• Molecular Formula: C14H17F2NO4
• Molecular Weight: 301.29
• DSSTox Substance ID: DTXSID601180926
• Mol file: 167993-07-9.mol

Synonyms:167993-07-9;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoic acid;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-2,6-difluoro-;N-Boc-2,6-Difluoro-L-phenylalanine;Boc-2,6-Difluoro-L-Phenylalanine;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(2,6-DIFLUOROPHENYL)PROPANOIC ACID;(2S)-3-(2,6-DIFLUOROPHENYL)-2-[(TERT-BUTOXY)CARBONYLAMINO]PROPANOIC ACID;SCHEMBL1529787;JQRFXXIFWMNGAG-NSHDSACASA-N;DTXSID601180926;CS-0434043;F78738;N-[(1,1-Dimethylethoxy)carbonyl]-2,6-difluoro-L-phenylalanine;2(S)-tert-butoxycarbonylamino-3-(2,6-difluorophenyl)-propionic acid;2(S)-tert-butoxycarbonylamino-3-(2,6-difluorophenyl)propionic acid;N-{[(1,1-dimethylethyl)oxy]carbonyl}-2,6-difluoro-L-phenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoicacid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoic acid

Chemical Property:

• 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:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=C(C=CC=C1F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=C(C=CC=C1F)F)C(=O)O

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoic acid

There total 5 articles about (S)-2-((tert-Butoxycarbonyl)amino)-3-(2,6-difluorophenyl)propanoic acid 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-2-amino-3-(2,6-difluorophenyl)propanoic acid (33787-05-2,266360-62-7) → N-{[(1,1-dimethylethyl)oxy]carbonyl}-2,6-difluoro-L-phenylalanine (167993-07-9,851047-82-0)

Guidance literature:

In 1,4-dioxane; water; at 0 - 20 ℃;

Reference yield:

2,6-Difluorobenzyl bromide (85118-00-9) → N-{[(1,1-dimethylethyl)oxy]carbonyl}-2,6-difluoro-L-phenylalanine (167993-07-9,851047-82-0)

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-(2,6-difluoro-phenyl)-propionic acid (266360-50-3) → N-{[(1,1-dimethylethyl)oxy]carbonyl}-2,6-difluoro-L-phenylalanine (167993-07-9,851047-82-0)

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

(2S)-2-amino-3-(2,6-difluorophenyl)propanoic acid

2,6-Difluorobenzyl bromide

2-acetylamino-3-(2,6-difluoro-phenyl)-propionic acid

Downstream raw materials:

(S)-tert-butyl (3-(2,6-difluorophenyl)-1-(methoxyamino)-1-oxopropan-2-yl)carbamate

1,1-dimethylethyl [(1S)-2-(2,6-difluorophenyl)-1-(hydroxymethyl)ethyl]carbamate