124980-98-9

Basic information

• Product Name: Methyl (R)-3-(4-Fluorophenyl)-2-hydroxypropionate
• Synonyms: Methyl (R)-3-(4-Fluorophenyl)-2-hydroxypropionate;(αR)-4-Fluoro-α-hydroxy-benzenepropanoic Acid Methyl Ester;-Methyl 3-(4-fluorophenyl);Methyl (R)-3-(4-Fluorophenyl)-2-Hydroxypropionate(WX618499)
• CAS NO: 124980-98-9
• Molecular Formula: C₁₀H₁₁FO₃
• Molecular Weight: 198
• Mol File: 124980-98-9.mol

Chemical Properties

• Boiling Point: 291.708 °C at 760 mmHg
• Flash Point: 130.221 °C
• Appearance: /
• Density: 1.232 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 12.67±0.20(Predicted)
• CAS DataBase Reference: Methyl (R)-3-(4-Fluorophenyl)-2-hydroxypropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (R)-3-(4-Fluorophenyl)-2-hydroxypropionate(124980-98-9)
• EPA Substance Registry System: Methyl (R)-3-(4-Fluorophenyl)-2-hydroxypropionate(124980-98-9)

Safety Data

• Hazardous Substances Data: 124980-98-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate is used as a reactant for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of antipicornaviral agents, which are essential for treating infections caused by picornaviruses, a family of RNA viruses that includes the common cold virus, rhinovirus, and poliovirus.
Additionally, it serves as a building block for the creation of rhinovirus protease inhibitors. These inhibitors are vital in the development of antiviral drugs that target the protease enzyme in rhinoviruses, thereby disrupting the virus's replication process and helping to combat infections.
Furthermore, Methyl (R)-3-(4-fluorophenyl)-2-hydroxypropionate is utilized in the preparation of agents for the treatment of chemokine-mediated diseases. Chemokines are small proteins that play a significant role in immune responses and inflammation. By targeting chemokine pathways, these agents can potentially alleviate the symptoms and progression of various diseases, including autoimmune disorders and chronic inflammatory conditions.

Upstream product

• 4538-50-5 methyl (2R)-glycidate 
• 352-13-6 4-flourophenylmagnesium bromide 
• 67-56-1 methanol 
• 124980-94-5 (2R)-3-(4-fluorophenyl)-2-hydroxypropanoic acid 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 921204-92-4 (R)-3-(4-fluorophenyl)-2-(4-nitrobenzenesulfonyloxy)propionic acid methyl ester 
• 328273-04-7 (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester 
• 223526-67-8 (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid 
• 862414-84-4 allyl (2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methyl-3-isoxazolyl)carbonyl]amino}-4-oxoheptanoate 
• 862414-82-2 allyl (2R,5S)-5-(tert-butoxycarbonyl)amino-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 328273-02-5 (2R,5S)-methyl 5-(benzyloxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 862414-80-0 (2R,5S)-methyl 5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 328086-55-1 (2R,5S)-2-(4-Fluoro-benzyl)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-4-oxo-heptanoic acid 
• 921204-93-5 (αS)-methyl 4-[[4-(3,4-dichlorophenoxy)-1-piperidinyl]methyl]-α-((4-fluorophenyl)methyl)-1-piperidineacetate 

Relevant articles and documents

Organocatalytic synthesis of optically active aryllactic acid derivatives from β-ketosulfoxides

The organocatalytic synthesis of new α-acyloxy-3-arylpropionic thioesters has been accomplished providing some enantioenriched important aryllactic acid derivatives in good yield and enantioselectivities.

Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters

The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.

Development of a continuous enzymatic process for the preparation of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid

While many methods have been reported for the synthesis of chiral 2-hydroxy acids, few of them have proven to be reliable toward the synthesis of the title compound in terms of overall yield and enantioselectivity. Herein we describe a continuous enzymatic process for an efficient synthesis of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid at multikilogram scale with a high space-time yield (560 g/(L·d)) using a membrane reactor. The product was generated in excellent enantiomeric excess (ee > 99.9%) and good overall yield (68-72%).