Organometallics in Process Chemistry by Rob Larsen

By Rob Larsen

The layout of effective syntheses of medicinal brokers is among the leading objectives of the method chemist within the pharmaceutical undefined. The increasing record of metal-mediated reactions has had a tremendous influence in this pastime over the past twenty years. This quantity will spotlight a few of the parts of organometallic chemistry that experience performed a very vital position in improvement. The chapters are written by way of chemists who paintings within the procedure teams of significant pharmaceutical businesses and high-quality chemical brands. Having proven the facility of organometallics of their procedures the authors herein extend upon their reviews with examples from the literature as stated through method teams in the undefined. The chapters are prepared both via the appliance of a selected steel or response type. elimination of the residual metal(s) from the remoted energetic pharmaceutical component (API) is vital to the discharge of the fabric for human intake, and therefore, is reviewed the following in addition. This quantity of themes in Organometallic Chemistry is gifted to supply a consultant pass part of organometallic functions within the pharmaceutical in addition to to offer an appreciation for the creativity attainable in strategy chemistry.

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54. 55. 56. 1007/b11770 Applications of Organotitanium Reagents David L. Hughes Department of Process Research, Merck and Co. com Abstract Organometallic transformations involving titanium are employed both catalytically and stoichiometrically in the pharmaceutical and fine chemical industry. The current review outlines a number of examples of the industrial applications of organotitanium reagents over the past decade. In addition, several reactions are briefly reviewed for which no industrial applications have been reported, but for which commercial utility may be envisaged.

The most important industrial application of the titanium-mediated asymmetric sulfoxidation is the production of the proton-pump inhibitor esomeprazole, (Nexium), the single enantiomer of omeprazole (Prilosec) [62]. (Scheme 22) As an effective treatment for acid-reflux and the prevention of ulcers, Prilosec was one of the top selling drugs in the world in 2001 (>$6 billion). 56 D. L. Hughes Scheme 22 The asymmetric oxidation of omeprazole sulfide 35 required significant modifications of the Kagan procedure in order to obtain the chiral sulfoxide 36 in high yield and ee in a process amenable for scale up.

The significant aspect of the Sharpless-Katsuki discovery was that the stereochemistry of the epoxidation product could be predicted and controlled based on which enantiomer of the reagent (tartrate) was used. Thus, the stereochemical information inherent in the reagent could be transferred to a pro-chiral substrate, and either product enantiomer could be generated depending on which reagent enantiomer was used in the reaction. This work led in part to the awarding of the Nobel Prize to Sharpless in 2001.

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