- FeCl3-catalyzed oxidative decarboxylation of aryl/heteroaryl acetic acids: Preparation of selected API impurities
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There is an ever-increasing demand for impurity compounds for use in impurity profiling as regulatory agencies seek information during registration. Herein, we report the FeCl3-catalyzed oxidative decarboxylation of aryl- and heteroaryl acetic acids to the corresponding carbonyl compounds. A variety of useful aldehydes and ketones were prepared in a simple one-pot transformation by employing an environmentally benign, low-cost, and readily available iron salt. The utility of this method has been demonstrated by preparing five valuable API impurities including a multi-gram-scale synthesis of ketorolac impurity B for the first time. This journal is
- Gangadurai, Chinnakuzhanthai,Illa, Giri Teja,Reddy, D. Srinivasa
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p. 8459 - 8466
(2020/11/05)
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- Photoredox-Catalyzed Decarboxylative Oxidation of Arylacetic Acids
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A photoredox-catalyzed decarboxylative oxidation of arylacetic acids, which are privileged scaffolds in pharmaceuticals, is reported herein. The established method is operationally simple and a variety of substrates are applicable, providing rapid access to dehomologated bioisosteres of common pharmaceuticals.
- Sakakibara, Yota,Cooper, Phillippa,Murakami, Kei,Itami, Kenichiro
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supporting information
p. 2410 - 2413
(2018/06/04)
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- Polystyrene-bound Mn(T4PyP): A highly efficient and reusable catalyst for biomimetic oxidative decarboxylation of carboxylic acids with sodium periodate
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In this report, highly efficient oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by a supported manganese(III) porphyrin is described. In the presence of manganese(III) tetra(4-pyridyl)porphyrin supported on cross-linked chloromethylated polystyrene, [Mn(T4PyP)-CMP], as catalyst, carboxylic acids were converted to their corresponding carbonyl compounds via oxidative decarboxylation with sodium periodate using imidazole as axial ligand. The oxidation of anti-inflammatory drugs such Indomethacin and Ibuprofen was carried out successfully and the decarboxylated products were obtained. This catalyst can be reused several times without loss of its catalytic activity in the oxidation reactions.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-baltork, Iraj,Sirjanian, Narges,Parand, Somayeh
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experimental part
p. 3394 - 3398
(2009/09/08)
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- Efficient oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by supported manganese (III) porphyrin
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Oxidative decarboxylation of carboxylic acids by a supported manganese (III) porphyrin was investigated. In the chemical system using 5,10,15,20-tetrakis(4-aminophenyl)porphyrinatomanganese (III) chloride supported on crosslinked chloromethylated polystyrene, [Mn(H 2NTPP)-CMP], as catalyst, carboxylic acids are converted to the corresponding carbonyl compounds via oxidative decarboxylation with sodium periodate.
- Mirkhani, Valiollah,Tangestaninejad, Shahram,Moghadam, Majid,Karimian, Zohreh
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p. 3433 - 3435
(2007/10/03)
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- Efficient and Mild Oxidative Decarboxylation of Aryl-substituted Carboxylic Acids by Iron and Manganese Porphyrin Periodate Systems
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The oxidative decarboxylation of α-aryl carboxylic acids to the corresponding carbonyl derivatives was observed in catalytic systems containing tetrabutylammonium periodate and metallotetraphenylporphyrins (metal = FeIII or MnIII) at room temperature.
- Tangestaninejad, Shahram,Mirkhani, Valiollah
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p. 820 - 821
(2007/10/03)
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- Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system
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The oxidative hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids by a chemical cytochrome P-450 model and rat liver microsomal systems has been investigated. In the chemical system using meso-tetrakis(2,6-dichlorophenyl)porphyrin iron chloride [Fe(TDClPP)Cl] with iodosylbenzene (PhIO), γ,δ-unsaturated carboxylic acids have been converted into δ-hydroxy-γ-lactones in high yield and with high stereoselectivity. As an example of a β,γ-unsaturated carboxylic acid, indomethacin has been converted into the corresponding β-hydroxy γ-lactone. Several experiments directed toward mechanistic elucidation of the lactonization exclude a mechanism occurring via an epoxide intermediate. The products have been used as standards to identify the metabolites in the microsomal oxidation. In the case of indomethacin, the γ-lactone form is detected as a metabolite in the rat liver microsomal system, in a yield of 1.33%; the yield is significantly decreased in the presence of 2-diethylaminoethyl-2,2-diphenylvalerate hydrochloride (SKF-525A) and under a mixed CO-O2 (4:1) atmosphere. Thus, these metabolites are considered to be formed by a cytochrome P-450-dependent reaction.
- Komuro, Masakatsu,Higuchi, Tsunehiko,Hirobe, Masaaki
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p. 2309 - 2313
(2007/10/03)
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- OXIDATIVE DECARBOXYLATION OF CARBOXYLIC ACIDS BY IRON PORPHYRIN - IODOSYLBENZENE SYSTEM
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An iodosylbenzene - iron tetraarylporphyrin catalyst system decarboxylated α-aryl carboxylic acids and α,α,α-trisubstituted acetic acids efficiently to give the corresponding alcohol and carbonyl derivatives.
- Komuro, Masakatsu,Nagatsu, Yoshio,Higuchi, Tsunehiko,Hirobe, Masaaki
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p. 4949 - 4952
(2007/10/02)
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