(R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid

Base Information

• Chemical Name: (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid
• CAS No.: 767352-29-4
• Molecular Formula: C17H16F3NO3
• Molecular Weight: 339.314
• Hs Code.: 2922509090
• Mol file: 767352-29-4.mol

Synonyms:(3R)-3-[(Benzyloxy)amino]-4-(2,4,5-trifluorophenyl)butanoic acid;benzenebutanoic acid, 2,4,5-trifluoro-β-[(phenylmethoxy)amino]-, (βR)-;

Chemical Property of (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid

Chemical Property:

• Refractive Index: 1.547
• Boiling Point: 456.7 °C at 760 mmHg
• Flash Point: 230 °C
• PSA: 58.56000
• Density: 1.329 g/cm³
• LogP: 3.60200
• Storage Temp.: 2-8°C

Purity/Quality:

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

(R)-3-((Benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid

There total 12 articles about (R)-3-(Benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoic 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: 93.0%

N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine (767352-30-7) → (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid (767352-29-4)

Guidance literature:

N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine; With water; lithium hydroxide; In tetrahydrofuran; at 0 ℃;

With sodium hydroxide; In tetrahydrofuran; water; pH=10;

With hydrogenchloride; In water; pH=5;

DOI:10.1016/j.ejmech.2010.08.002

Reference yield: 78.0%

N-benzyloxyamine (622-33-3) + (E)-4-(2,4,5-trifluorophenyl)but-2-enoic acid → (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid (767352-29-4)

Guidance literature:

With C₂₁H₂₈BN₃O₂S; benzoic acid; at 20 ℃; for 48h; enantioselective reaction; Molecular sieve;

DOI:10.1021/jacs.8b07511

Reference yield:

methanesulfonic acid (75-75-2,98527-29-8) + C16H12F3NO2 → (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid (767352-29-4)

Guidance literature:

C₁₆H₁₂F₃NO₂; With lithium hydroxide monohydrate; In tetrahydrofuran; at 20 ℃; for 2h;

methanesulfonic acid; In tetrahydrofuran; at 10 ℃;

upstream raw materials:

N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine

methyl 3-(benzyloxyamino)-4-(2,4,5-trifluorophenyl) butanoate

(E)-4-(2,4,5-trifluoro-phenyl)-but-2-enoic acid methyl ester

(R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid (R)-(+)-N-benzyl-α-methylbenzylamine salt

Downstream raw materials:

(3R)-3-(benzyloxyamino)-1-[hexahydro-3-oxo-oxazolo[3,4-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

(3R)-3-(benzyloxyamino)-1-[hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

(3R)-3-(benzyloxyamino)-1-[2-benzyl-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

Refernces

• 1、 Hayama, Noboru,Kuramoto, Ryuta,F?ldes, Tamás,Nishibayashi, Kazuya,Kobayashi, Yusuke,Pápai, Imre,Takemoto, Yoshiji. "Mechanistic Insight into Asymmetric Hetero-Michael Addition of α,β-Unsaturated Carboxylic Acids Catalyzed by Multifunctional Thioureas". supporting information. p. 12216 - 12225. Retrieved 2018/09/25.
• 2、 -. "PREPARATION OF OPTICALLY PURE ?-AMINO ACID TYPE ACTIVE PHARMACEUTICAL INGREDIENTS AND INTERMEDIATES THEREOF". Page/Page column 28. . Retrieved 2013/07/25.