methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate

Base Information

• Chemical Name: methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate
• CAS No.: 1213132-66-1
• Molecular Formula: C₁₀H₁₀F₃NO₂
• Molecular Weight: 233.19
• Mol file: 1213132-66-1.mol

Synonyms:methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate

Chemical Property of methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate

There total 3 articles about methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate 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:

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine (486460-07-5) → methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate (1213132-66-1)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; for 72h;

Reference yield:

2,4,5-trifluorobenzaldehyde (165047-24-5) → methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate (1213132-66-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: D-glucose; nicotinamide adenine dinucleotide phosphate; glucose dehydrogenase from Bacillus megaterium; ene-reductase OYE₃ from Saccharomyces cerevisiae / dimethyl sulfoxide; aq. phosphate buffer / 120 h / 30 °C / pH 7.0 / Enzymatic reaction

3.1: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate

With N-Bromosuccinimide; sodium azide; D-glucose; glucose dehydrogenase from Bacillus megaterium; palladium 10% on activated carbon; ene-reductase OYE₃ from Saccharomyces cerevisiae; hydrogen; nicotinamide adenine dinucleotide phosphate; In tetrahydrofuran; aq. phosphate buffer; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c9gc01902b

Reference yield:

methyl (Z)-2-bromo-3-(2,4,5-trifluorophenyl)acrylate → methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate (1213132-66-1)

Guidance literature:

Multi-step reaction with 3 steps

1: D-glucose; nicotinamide adenine dinucleotide phosphate; glucose dehydrogenase from Bacillus megaterium; ene-reductase OYE₃ from Saccharomyces cerevisiae / dimethyl sulfoxide; aq. phosphate buffer / 120 h / 30 °C / pH 7.0 / Enzymatic reaction

2: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C

3: palladium 10% on activated carbon; hydrogen / ethyl acetate

With sodium azide; D-glucose; glucose dehydrogenase from Bacillus megaterium; palladium 10% on activated carbon; ene-reductase OYE₃ from Saccharomyces cerevisiae; hydrogen; nicotinamide adenine dinucleotide phosphate; In aq. phosphate buffer; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c9gc01902b

upstream raw materials:

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine

2,4,5-trifluorobenzaldehyde

Downstream raw materials:

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate

Refernces

• 1、 -. "PIPERIDINO PYRIMIDINE DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OF DIABETES". Page 44. . Retrieved 2008/06/13.