23981-80-8Relevant articles and documents
Racemization and hydrolysis of (S)-naproxen 2,2,2-trifluoroethyl ester in non-polar solvents by strong neutral bases: Implication for ion-pair kinetic basicity and hydrolysis
Lin, Man-Yuan,Lay, Eddy,Wen, Wen-Yen,Dewi, Hamza,Cheng, Yu-Chi,Tsai, Shau-Wei
, p. 387 - 392 (2004)
By using strong neutral bases as catalyst, a detailed investigation of the racemization of (S)-naproxen 2,2,2-trifluoroethyl ester was conducted in the non-polar solvents isooctane, cyclohexane and n-hexane. The second-order interconversion constant kint* as representing the ion-pair kinetic basicity in isooctane was first estimated and correlated with the equilibrium ion-pair basicity pKip in tetrahydrofuran, giving slopes of 0.768 and 0.689 for non-phosphazene and phosphazene bases, respectively, in the Bronsted correlations. The result was further compared with that for (S)-naproxen 2,2,2-trifluoroethyl thioester, showing about a 1-2 orders of magnitude enhancement of kint* for the corresponding thio-containing analogue. A smaller influence of non-polar solvents (i.e. isooctane, n-hexane and cyclohexane) on kint* was found. Kinetic analysis of the racemization and hydrolysis of (S)-naproxen 2,2,2-trifluoroethyl ester in isooctane and n-hexane containing 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene and water suggests nucleophilic hydrolysis by the base, where the breakdown of tetrahedral intermediates I R1 and IS1 is the rate-limiting step and the hydrolysis constant khy is in proportion to the product of base and ion-pair concentrations. Copyright 2004 John Wiley & Sons, Ltd.
Simple synthetic approach to arylacetic NSAIAs via TosMIC procedure
Di Santo,Costi,Massa,Artico
, p. 787 - 793 (1995)
Preparation of 1-methylpyrrole-2-acetonitrile, 1-methyl-5-(4-methylbenzoyl) pyrrole-2-acetonitrile and 2-(6-methoxy-2-naphthyl)propionitrile by treatment of 1-methylpyrrole-2-carboxaldehyde, 1-methyl-5-(4-methylbenzoyl)pyrrole-2-carboxaldehyde and, respectively, 6-methoxy-2-acetylnaphthalene with tosylmethylisocyanide (TosMIC) is described. This one-step synthetic procedure is very useful to obtain the nitrile precursors of tolmetin and naproxen, two clinically important non-steroidal antiinflammatory agents (NSAIAs).
Naproxen impurity and preparation method thereof
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Paragraph 0033; 0039, (2021/02/06)
The invention provides a naproxen impurity R, and the structural formula of the naproxen impurity R is shown in the specification. The invention also provides a preparation method of the naproxen impurity R. The preparation method comprises the following steps of: demethylating naproxen racemate in an acidic medium, and further reacting the demethylated naproxen racemate with 3-bromo-2, 2-dimethyl-1-propanol in the presence of an acid-binding agent to obtain the naproxen impurity R. The naproxen impurity R disclosed by the invention is suitable for being used as an impurity reference substancefor researching the synthesis quality of naproxen and intermediates thereof.
Preparation of One-Pot Immobilized Lipase with Fe3O4 Nanoparticles Into Metal-Organic Framework For Enantioselective Hydrolysis of (R,S)-Naproxen Methyl Ester
Ozyilmaz, Elif,Ascioglu, Sebahat,Yilmaz, Mustafa
, p. 3687 - 3694 (2021/06/25)
Immobilization of enzyme to magnetic metal-organic frameworks (MOF) can preserve biological functionality in harsh environments to increase enzymes activity, stability, and improve reusability. The magnetic Fe3O4 nanoparticles were treated with calix[4]arene tetracarboxylic acid (Calix) and Candida rugosa lipase (CRL), and then encapsulated into the zeolitic imidazole framework-8 (Fe3O4@Calix-ZIF-8@CRL). The lipase activity data of Fe3O4@Calix-ZIF-8@CRL was 2.88 times higher than that of the Fe3O4@ZIF-8@CRL (without Calix). The catalytic properties of immobilized lipases were studied on the enantioselective hydrolysis of R/S-naproxen methyl ester. It was also observed that Fe3O4@Calix-ZIF-8@CRL has excellent enantioselectivity (E=371) compared to Fe3O4@ZIF-8@CRL (E=131). Furthermore, Fe3O4@Calix-ZIF-8@CRL was seen to still retain 30 % of the conversion rate after the fifth reuse. This work may also be useful for the pharmaceutical industry due to the increased reusability and stability of enzymes, the enantiomeric selectivity exhibited by MOF-enzyme biocomposites, and the significant differences in the biological activities of the enantiomers.
Method for synthesizing aryl propionic acid by metal-free catalysis of carbon dioxide carboxylation
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Paragraph 0065-0067, (2021/02/10)
The invention relates to the field of carbon dioxide immobilization and conversion, and particularly discloses a method for synthesizing aryl propionic acid by metal-free catalysis of carbon dioxide carboxylation. The method comprises the following steps: stirring a mixed solution of a diselenide catalyst and a styrene compound in a carbon dioxide atmosphere, adding hydrogen peroxide, and stirringto react, thereby obtaining the aryl propionic acid. Styrene is directly used as a raw material, diselenide is used as a catalyst to realize a carboxylation reaction of olefin and carbon dioxide, andcompared with metal catalyst residues or halogen-containing byproducts in a traditional synthesis method, the byproducts in the method only contain water, and small molecular diselenide is used as the catalyst to replace the traditional metal catalyst, and metal residuals are avoided.
