56374-24-4

Upstream product

• 6814-64-8 methylenedimethyl sulfurane 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 41343-01-5 2-(p-isobutylphenyl)-1,2-propanediol 
• 34352-86-8 1-isobutyl-4-(prop-1-en-2-yl)benzene 
• 182816-13-3 1-bromo-2-(4-isobutylphenyl)propan-2-ol 
• 75-18-3 dimethylsulfide 

Downstream Products

• 114937-30-3 (2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol 
• 51407-46-6 2-(4-isobutylphenyl)propionaldehyde 
• 180293-49-6 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionic acid 
• 51146-56-6 (S)-ibuprofen 
• 159850-44-9 (S)-2-(4-isobutylphenyl)-1,2-propanediol 
• 171417-12-2 (R)-2-(p-isobutylphenyl)-1,2-propanediol 
• 41343-01-5 2-(p-isobutylphenyl)-1,2-propanediol 
• 182816-19-9 2-fluoro-2-(4-isobutylphenyl)propanol 

Relevant academic research and scientific papers

Microbiological transformations 43. Epoxide hydrolases as tools for the synthesis of enantiopure α-methylstyrene oxides: A new and efficient synthesis of (S)-ibuprofen

Biohydrolysis of various α-methylstyrene oxide derivatives, differently substituted at the aromatic ring, was investigated using 10 epoxide hydrolases from different origins. Our results indicate that the enantioselectivity of these biohydrolyses strongly depends on the nature of the enzyme and of the substituent. Using some of these enzymes, this approach allows to prepare these epoxides in high optical purity. The potentiality to perform efficient preparative-scale resolution using such a biocatalyst was illustrated by the four-step synthesis of (S)-ibuprofen, a nonsteroidal antiinflammatory drug and household pain killer, one of the top-ten drugs sold worldwide. Using a combined chemoenzymatic strategy, we were thus able to set up a four-step enantioconvergent procedure allowing for the synthesis of this compound in optically pure form and with a 47% overall yield, including the resolution process, due to a possible recycling of the formed diol via chemical racemisation.

Convenient routes to 2-aryl-2-fluoropropionic acids: Synthesis of monofluorinated analogues of (±)-ibuprofen, (±)-naproxen and related compounds

The synthesis of α-fluorinated arylpropionic acids 5 as analogues of the nonsteroidal anti-inflammatory agents (NSAIDs) flurbiprofen 1, ibuprofen 3 and naproxen 4 is accomplished by the oxidation of the corresponding primary alcohols 9. The latter are accessible on two different pathways showing their general applicability by variation of the aromatic moiety. Furthermore the influence of the fluorine substituent towards the conformation of the acid moiety in the crystal lattice is shown by comparative X-ray studies of compound 5c.

Enantioselective hydrolysis of 2,2-disubstituted oxiranes mediated by microsomal epoxide hydrolase

2-Aryl-2-methyloxiranes are enantioselectively hydrolyzed with microsomal epoxide hydrolase from pig liver to provide 1,2-diols containing a tertiary benzylic alcohol stereogenic centre upto 34% enantiomeric purities.

Method for producing 2-(substituted aryl) propionaldehyde

A 2-(substituted aryl)propionaldehyde of the formula, STR1 (wherein Ar denotes STR2 is produced in high yield by reacting a methyl (substituted aryl) ketone of the formula STR3 with phenyldimethylsulfonium methylsulfate of the formula, STR4 in the presence of alkali metal hydroxide to obtain a reaction mixture containing 2-(substituted aryl)1,2-epoxypropane of the formula, STR5 and thioanisole, and subjecting the reaction mixture to contact with anhydrous MgCl2. The propionaldehyde compound is also produced in high yield by contacting the epoxypropane compound with anhydrous MgCl2 in the presence of a soft nucleophile such as a sulfide, a thiol and a phosphine.