- CONTINUOUS FLOW SYNTHESIS OF IBUPROFEN
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This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
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Paragraph 0018; 0020-0021; 0366; 0381-0384; 0388-0391
(2021/04/23)
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- Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group
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The oxetane ring serves as an isostere of the carbonyl moiety, suggesting that oxetan-3-ol may be considered as a potential surrogate of the carboxylic acid functional group. To investigate this structural unit, as well as thietan-3-ol and the corresponding sulfoxide and sulfone derivatives, as potential carboxylic acid bioisosteres, a set of model compounds has been designed, synthesized, and evaluated for physicochemical properties. Similar derivatives of the cyclooxygenase inhibitor, ibuprofen, were also synthesized and evaluated for inhibition of eicosanoid biosynthesis in vitro. Collectively, the data suggest that oxetan-3-ol, thietan-3-ol, and related structures hold promise as isosteric replacements of the carboxylic acid moiety.
- Lassalas, Pierrik,Oukoloff, Killian,Makani, Vishruti,James, Michael,Tran, Van,Yao, Yuemang,Huang, Longchuan,Vijayendran, Krishna,Monti, Ludovica,Trojanowski, John Q.,Lee, Virginia M.-Y.,Kozlowski, Marisa C.,Smith, Amos B.,Brunden, Kurt R.,Ballatore, Carlo
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supporting information
p. 864 - 868
(2017/08/16)
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- MgCl2-accelerated addition of functionalized organozinc reagents to aldehydes, ketones, and carbon dioxide
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Figure Presented Pump it up! The sluggish reactivity of organozinc reagents in additions to aldehydes, ketones, and CO2 can be increased by MgCl2, which is usually generated in the preparation of the zinc reagent. The direct reaction with CO2, in particular, opens an expeditious route to phenylacetic acid derivatives, as demonstrated in a short synthesis of ibuprofen (see scheme).
- Metzger, Albrecht,Bernhardt, Sebastian,Manolikakes, Georg,Knochel, Paul
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supporting information; experimental part
p. 4665 - 4668
(2010/08/19)
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- Process for the carbonylation of arylalkyl halides
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A method is provided for the preparation of alpha-aryl-propionic acids such as ibuprofen by carbonylating the corresponding 1-arylethyl halide in an acidic aqueous medium containing a palladium catalyst. In the preparation of ibuprofen, 1-(4′-isobutylphenyl)ethyl halide is reacted with carbon monoxide in an acidic aqueous medium containing a palladium catalyst.
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- Synthesis of E-aryl ethenesulfonamides: A simple one-pot, two-step procedure from 1-hydroxy-1-arylalkanes
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The unusual reactivity of 1-phenyl-1-ethane-sulfonic acid in thionyl chloride was investigated. Mechanistic considerations led us to set up a new and efficient synthesis of E-arylethenesulfonamides starting from 1-hydroxy-1-arylalkanes. The easy availability of the starting materials and the straightforward, one-pot procedure make this process an attractive method for the preparation of these compounds currently largely employed in chemical and pharmaceutical fields.
- Aramini, Andrea,Cesta, Maria C.,Coniglio, Silvia,Bijani, Christian,Colagioia, Sandro,D'Elia, Valerio,Allegretti, Marcello
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p. 7911 - 7914
(2007/10/03)
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- Performances of homogeneous charge transfer catalysts in the electrocarboxylation of benzyl halides
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The electrocarboxylation of benzyl halides to the corresponding carboxylic acids performed by homogeneous charge transfer catalysts is reported here. The performances of selected ester derivatives of benzoic acid and of the three isomers of benzenedicarboxylic acid as catalysts are evaluated on the basis of the faradaic efficiency of the carboxylation and of the decomposition rate of the catalyst. The standard redox potentials of catalysts are related to the selectivity of the process. Rates of catalyst decomposition appear to be dependent on the molar ratio [halide]/[catalyst] and on the cathode material.
- Scialdone, Onofrio,Filardo, Giuseppe,Galia, Alessandro,Mantione, Davide,Silvestri, Giuseppe
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p. 800 - 806
(2007/10/03)
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- Biomimetic oxidation of ibuprofen with hydrogen peroxide catalysed by Horseradish peroxidase (HRP) and 5,10,15,20- tetrakis-(2',6'-dichloro-3'- sulphonatophenyl)porphyrinatoiron(III) and manganese(III) hydrates in AOT reverse micelles
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The oxidation of ibuprofen with H2O2 catalysed by Horseradish peroxidase (HRP), Cl8TPPS4Fe(III)(OH2)2 and Cl8TPPS4Mn(III)(OH2)2 in AOT reverse micelles gives 2-(4'-isobutyl-phenyl)ethanol (5) and p-isobutyl acetophenone (6) in moderate yields. The reaction of ibuprofen (2) with H2O2 catalysed by HRP form carbon radicals by the oxidative decarboxylation, which on reaction with molecular oxygen to form hydroperoxy intermediate, responsible for the formation of the products 5 and 6. The yields of different oxidation products depend on the pH, the water to surfactant ratio (Wo), concentration of Cl8TPPS4Fe(III)(OH2)2 and Cl8TPPS4Mn(III)(OH2)2 and amount of molecular oxygen present in AOT reverse micelles. The formation of 2-(4'-isobutyl phenyl)ethanol (5) may be explained by the hydrogen abstraction from ibuprofen by high valent oxo- manganese(IV) radical cation, followed by decarboxylation and subsequent recombination of either free hydroxy radical or hydroxy iron(III)/manganese(III) porphyrins. The over-oxidation of 5 with high valent oxo-manganese, Mn(IV)radical cation intermediate form 6 in AOT reverse micelles by abstraction and recombination mechanism. (C) 1999 Elsevier Science Ltd.
- Chauhan,Sahoo
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p. 2629 - 2634
(2007/10/03)
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- Preparation of aryl-substituted olefins
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A process for dehydrohalogenation of aryl-substituted aliphatic halohydrocarbons is disclosed. The process employs a catalytically effective amount of palladium(0) and a phosphorus-containing ligand. An inorganic or organic base is also required to effect this reaction.
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- Chiral (β-Aminoalkyl)phosphines. Highly Efficient Phosphine Ligands for Catalytic Asymmetric Grignard Cross-Coupling
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New chiral (β-aminoalkyl)phosphines, RCH(NMe2)CH2PPh2 , were prepared by starting with optically active amino acids.The phosphines were used as ligands for nickel-catalyzed asymmetric cross-coupling of 1-arylethyl Grignard reagents (ArMeCHMgCl) with vinyl bromide.Coupling products of over 70percent enantiomeric excess (ee) were obtained in the reaction with the ligand Phephos, Valphos, Ilephos, PhGlyphos, ChGlyphos, or t-Leuphos.A mechanism involving complexation of the magnesium atom in the Grignard reagent with the amino group on the (β-aminoalkyl)phosphine ligand is proposed to account for the high stereoselectivity.The asymmetric cross-coupling was applied to the synthesis of optically active 2-arylpropionic acids.
- Hayashi, Tamio,Konishi, Mitsuo,Fukushima, Motoo,Kanehira, Koichi,Hioki, Takeshi,Kumada, Makoto
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p. 2195 - 2202
(2007/10/02)
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