Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate

Base Information

• Chemical Name: Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate
• CAS No.: 124980-98-9
• Molecular Formula: C10H11FO3
• Molecular Weight: 198.19
• Hs Code.: 2918199890
• Mol file: 124980-98-9.mol

Synonyms:Methyl (2R)-3-(4-fluorophenyl)-2-hydroxy-propanoate;Benzenepropanoic acid, 4-fluoro-α-hydroxy-, methyl ester, (αR)-;(R)-Methyl 3-(4-fluorophenyl)-2-hydroxypropanoate;

Chemical Property of Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate

Chemical Property:

• Boiling Point: 291.708 °C at 760 mmHg
• PKA: 12.67±0.20(Predicted)
• Flash Point: 130.221 °C
• PSA: 46.53000
• Density: 1.232 g/cm³
• LogP: 0.90210
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%min ^*data from raw suppliers

(αR)-4-Fluoro-α-hydroxy-benzenepropanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl (R)-3-(4-Fluorophenyl)-2-hydroxypropionate is a reactant used in the preparation of antipicornaviral agents, rhinovirus protease inhibitors and agents for treatment of chemokine mediated diseases.

Technology Process of Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate

There total 4 articles about Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate 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: 86.0%

methyl (2R)-glycidate (4538-50-5,85485-00-3,118712-39-3,111058-32-3) + 4-flourophenylmagnesium bromide (352-13-6) → (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate (124980-98-9)

Guidance literature:

With CuBr-Me₂S; In tetrahydrofuran; at -35 ℃; for 1h;

DOI:10.1016/j.bmc.2005.05.065

Reference yield: 70.0%

methanol (67-56-1) + 3-(4-fluorophenyl)-1-oxo-1-(phenylthio)propan-2-yl acetate → (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate (124980-98-9)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 4h;

DOI:10.1080/17415993.2014.946506

Reference yield:

4-fluorobenzaldehyde (459-57-4) → (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate (124980-98-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: water / 10 h / Reflux

1.2: Reflux

2.1: NAD; formate dehydrogenase from Candida boidinii; D-lactate dehydrogenase from Staphylococcus epidermidis; ethylenediaminetetraacetic acid; 2-hydroxyethanethiol; ammonium formate; hydrogenchloride / water / pH 6.3 / Inert atmosphere; Enzymatic reaction

3.1: hydrogenchloride

With hydrogenchloride; ethylenediaminetetraacetic acid; formate dehydrogenase from Candida boidinii; D-lactate dehydrogenase from Staphylococcus epidermidis; NAD; ammonium formate; 2-hydroxyethanethiol; In water;

DOI:10.1021/op010232y

upstream raw materials:

methyl (2R)-glycidate

4-flourophenylmagnesium bromide

methanol

(2R)-3-(4-fluorophenyl)-2-hydroxypropanoic acid

Downstream raw materials:

(2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester

(R)-3-(4-fluorophenyl)-2-(4-nitrobenzenesulfonyloxy)propionic acid methyl ester

(αS)-methyl 4-[[4-(3,4-dichlorophenoxy)-1-piperidinyl]methyl]-α-((4-fluorophenyl)methyl)-1-piperidineacetate

(2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid

Refernces

• 1、 Shie, Jiun-Jie,Fang, Jim-Min,Kuo, Tun-Hsun,Kuo, Chih-Jung,Liang, Po-Huang,Huang, Hung-Jyun,Wu, Yin-Ta,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Wong, Chi-Huey. "Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters". . p. 5240 - 5252. Retrieved 2007/10/03.