73590-58-6Relevant articles and documents
Monitoring and Quantification of Omeprazole Synthesis Reaction by In-Line Raman Spectroscopy and Characterization of the Reaction Components
?ahni?, Damir,Me?trovi?, Ernest,Jedna?ak, Tomislav,Habinovec, Iva,Parlov Vukovi?, Jelena,Novak, Predrag
, p. 2092 - 2099 (2016)
The development of a quantitative in-line Raman spectroscopic method for the monitoring of the active pharmaceutical ingredient, omeprazole synthesis reaction, and characterization of the reaction components is described. In-line monitoring was performed both with Fourier transform and dispersive Raman spectrometers. Prior to reaction monitoring, the reaction components were characterized off-line by means of Raman and NMR spectroscopy, both in solution and in solid state. To unequivocally confirm the presence of each component in the reaction mixture, a state of the art LC-SPE/NMR methodology was also used. Owing to its higher sensitivity, dispersive Raman spectroscopy was further employed for quantification purposes. The spectroscopic measurements and the complementary HPLC analyses, used in the calibration development, were gathered from a set of experiments, performed at a 1 L scale. On the basis of the data set obtained from the calibration experiments, a predictive partial least-squares (PLS) regression model was developed for all three reaction components, enabling an accurate determination of the percentage of each component present in the reaction mixture, at any time after the point when 25% of the starting material has been consumed. The model was successfully used to monitor the reaction progress in a kilo-lab scale experiment and can further be used as a fast response analytical tool in process optimization. It also has the potential to be used as part of a feedback control loop in the production plant.
Synthetic method and application of omeprazole
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Paragraph 0045; 0048-0049; 0051-0054, (2021/07/17)
The invention belongs to the field of medicine synthesis, and discloses a synthetic method of omeprazole. The synthetic method comprises the following steps: reacting sodium (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinate to generate (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinic acid acyl chloride, and then carrying out Suzuki reaction on the (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinic acid acyl chloride and (6-methoxy-1H-benzo [d] imidazole-2-yl) boric acid to generate omeprazole. According to the synthetic method of omeprazole, the omeprazole which is easy to purify and stable in yield is obtained by using raw materials which are easy to obtain, and a synthetic method which is simple, easy to operate and control, mild in reaction condition and capable of replacing high-risk reagents such as butyl lithium and the like by using a common reagent. The invention also provides an application of the synthetic method of omeprazole. The synthetic method is suitable for synthesis of omeprazole. The obtained omeprazole is used for preparing an omeprazole injection.
Integrating hydrogen production with anodic selective oxidation of sulfides over a CoFe layered double hydroxide electrode
Ma, Lina,Zhou, Hua,Xu, Ming,Hao, Peipei,Kong, Xianggui,Duan, Haohong
, p. 938 - 945 (2021/02/06)
Replacing the sluggish oxygen evolution reaction (OER) with oxidation reactions for the synthesis of complex pharmaceutical molecules coupled with enhanced hydrogen evolution reaction (HER) is highly attractive, but it is rarely explored. Here, we report an electrochemical protocol for selective oxidation of sulfides to sulfoxides over a CoFe layered double hydroxide (CoFe-LDH) anode in an aqueous-MeCN electrolyte, coupled with 2-fold promoted cathodic H2productivity. This protocol displays high activity (85-96% yields), catalyst stability (10 cycles), and generality (12 examples) in selective sulfide oxidation. We demonstrate its applicability in the synthesis of four important pharmaceutical related sulfoxide compounds with scalability (up to 1.79 g). X-ray spectroscopy investigations reveal that the CoFe-LDH material evolved into amorphous CoFe-oxyhydroxide under catalytic conditions. This work may pave the way towards sustainable organic synthesis of valuable pharmaceuticals coupled with H2production.
Synthesis method of esomeprazole sodium
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, (2021/10/20)
The invention discloses a synthesis method of esomeprazole sodium. Belong to organic synthesis field. Of 5 - methoxy -2-mercaptobenzimidazole in ethanol - sodium hydroxide solution react with 2 - chloromethyl -3 and 5 -dimethyl -4 - methoxypyridine hydrochloride to obtain omeprazole thioether. The synthetic method is high in raw material utilization rate, reduces the content and kinds of impurities, greatly improves the extraction rate of esomeprazole sodium, can reach 75%, and has a purity of more than 99%. The synthetic route is short, and the synthesis cost is greatly reduced.
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
supporting information, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu
supporting information, p. 8691 - 8695 (2021/10/22)
A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.
Preparation method of omeprazole and omeprazole
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Paragraph 0049-0084, (2021/04/21)
The invention is applicable to the technical field of medicines, and provides a preparation method of omeprazole and omeprazole, and the preparation method comprises the following steps: dropwise adding a catalyst solution containing ammonium molybdate and hydrogen peroxide into a methanol solution of a thioether intermediate in sequence, and controlling the oxidation reaction temperature to -5-10 DEG C for reaction to obtain an omeprazole reaction solution; and adding sodium sulfite and a sodium hydroxide aqueous solution into the omeprazole reaction solution, uniformly mixing, dropwise adding an acetic acid aqueous solution, adding omeprazole seed crystals, stirring, continuously dropwise adding the acetic acid aqueous solution to adjust the pH value to 7.0-9.0, and adjusting the crystallization endpoint temperature to 10-20 DEG C, thereby obtaining the omeprazole crystal. The one-pot method of reaction and refining in the same solvent system is adopted, convenience of production operation is remarkably improved, operation steps are reduced, production energy consumption and time cost are reduced, and in addition, by optimizing all key parameters, the high-yield and high-purity omeprazole preparation process is achieved. The total yield of 25kg-grade production and preparation reaches 91.1%, the purity is 99.99%, and the method is superior to the pharmacopeia standard.
Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis
Li, Yiming,Rizvi, S. Aal-e-Ali,Hu, Deqing,Sun, Danwen,Gao, Anhui,Zhou, Yubo,Li, Jia,Jiang, Xuefeng
supporting information, p. 13499 - 13506 (2019/08/21)
Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late-stage oxygenation of sulfur-containing complex molecules with ground-state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO22+) enabled the efficient synthesis of sulfones. The ligand-to-metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a UV center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late-stage oxygenation in an atom- and step-efficient manner.
Tartaric acid ester compound as well as preparation method and applications thereof
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Paragraph 0101-0106, (2019/03/29)
The invention discloses a compound shown in formula (I), wherein R1 and R2 are independently selected from optionally substituted C1-6 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted C6-14 aryl and optionally substituted -(CH2)m-C3-8 cycloalkyl or -(CH2)n Ar; and Ar denotes the optionally substituted C6-14 aryl. The compound can be used for preparing prazole drugs during thetitanium-catalyzed asymmetric oxidation of pyrazole sulfides. (img file='DDA0001401304200000011.TIF' wi='669' he='551'/).
Sulfoxide and sulfone compounds, as well as selective synthesis method and application thereof
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Paragraph 0045-0048; 0190-0193, (2019/12/02)
The invention discloses a method for selectively synthesizing a sulfoxide compound shown as a formula (II) and a sulfone compound shown as a formula (III). In a reaction solvent, thioether (I) is usedas a reaction raw material and oxygen as an oxidation reagent, under the catalytic action of visible light and a photosensitive reagent; under the assistance of an additive, when a large-polarity proton-containing additive such as an acid and an alcohol or a solvent or an additive with excellent electron donating ability is used, a sulfoxide compound (II) is selectively generated; and when a small-polarity aprotic additive or a solvent is used, a sulfone compound (III) is selectively generated. The synthesis method has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some medicines are realized, and an efficient method for selectively constructing sulfoxide and sulfone compounds is provided for medicinal chemistry research.
