Chemical Process Research Research Articles

The Synthesis of N-Aryl-5(S)-aminomethyl-2-oxazolidinone Antibacterials and Derivatives in One Step from Aryl Carbamates

Since 1993, a significant process research and development effort directed towards the large-scale synthesis of oxazolidinone antibacterial agents has been ongoing in both Early Chemical Process Research and Development, and Chemical Process Research and Development at Pharmacia. This work has led to the successful development of the current commercial process to produce Zyvox (linezolid), recently approved by the FDA as an antibacterial. While this synthesis is appropriate for the preparation of linezolid in particular, a more convergent and versatile synthesis was developed for the rapid preparation of numerous other oxazolidinone analogues. Toward this end, economical methods for the large-scale preparation of N-[(2S)-2-(acetyloxy)-3-chloropropyl]acetamide 3 and tert-butyl [(2S)-3-chloro-2-hydroxypropyl]carbamate 27 from commercially available (S)-epichlorohydrin via the common intermediate (2S)-1-amino-3-chloro-2-propanol hydrochloride 2a were developed. Also, general methods for coupling these reagen...

R&D Intensification in Polymer Catalyst and Product Development by Using High‐Throughput Experimentation and Simulation

AbstractCurrently laboratory automation is a rapidly growing field of interest in chemical process research and development. The idea of using automated and parallel methods for the optimization of chemical processes was initiated by the extensive implementation of combinatorial techniques in medicinal chemistry. The techniques applied involve all methods and concepts aimed at dramatically increasing the output of research by extensive use of automation, parallelization and miniaturization, fast analysis, advanced data handling and by efficient automated planning, scheduling and tracking. In this paper, the “Combi” or high‐throughput experimentation approach consists of the integration of parallel experimentation with four key modeling and simulation methodologies, modeling, multivariate statistics, statistical design of experimentation and empirical model generation. Integrated automated liquid and solid handling.magnified imageIntegrated automated liquid and solid handling.

Synthesis of Injectable Antifungal Sch 59884

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of Injectable Antifungal Sch 59884Gary M. Lee, Jefrey Eckert, Dinesh Gala, Martin Schwartz, Paul Renton, Edward Pergamen, Michael Whttington, Doris Schumacher, Larry Heimark, and Petia ShipkovaView Author Information Chemical Process Research and Development, Schering-Plough Research Institute, 1011 Morris Avenue, Union, New Jersey 07083, U.S.A. Cite this: Org. Proc. Res. Dev. 2001, 5, 6, 622–629Publication Date (Web):October 12, 2001Publication History Received23 April 2001Published online12 October 2001Published inissue 1 November 2001https://doi.org/10.1021/op010212wCopyright © 2001 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views686Altmetric-Citations8LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (113 KB) Get e-AlertsSUBJECTS:Antimicrobial agents,Impurities,Reagents,Salts,Sodium Get e-Alerts

Reversible Michael reaction-enzymatic hydrolysis: a new variant of dynamic resolution.

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTReversible Michael Reaction−Enzymatic Hydrolysis: A New Variant of Dynamic ResolutionJaan A. Pesti, Jianguo Yin, Lin-hua Zhang, and Luigi AnzaloneView Author Information Chemical Process Research and Development Bristol-Myers Squibb Co. Chambers Works, Deepwater, New Jersey 08023 Cite this: J. Am. Chem. Soc. 2001, 123, 44, 11075–11076Publication Date (Web):October 11, 2001Publication History Received25 July 2001Published online11 October 2001Published inissue 1 November 2001https://doi.org/10.1021/ja011811lCopyright © 2001 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views662Altmetric-Citations23LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (31 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Hydrolysis,Molecular structure,Peptides and proteins,Phosphates,Stereoselectivity Get e-Alerts

Oxidative cleavage of 1,3-dicarbonyls to carboxylic acids with oxone.

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTOxidative Cleavage of 1,3-Dicarbonyls to Carboxylic Acids with OxoneScott W. Ashford and Kevin C. GregaView Author Information Chemical Process Research and Development, 1500-91-201, Pharmacia, Kalamazoo, Michigan 49001 [email protected]Cite this: J. Org. Chem. 2001, 66, 4, 1523–1524Publication Date (Web):January 19, 2001Publication History Received6 November 2000Published online19 January 2001Published inissue 1 February 2001https://doi.org/10.1021/jo001579mCopyright © 2001 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1319Altmetric-Citations43LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (40 KB) Get e-AlertsSUBJECTS:Alkyls,Anions,Bond cleavage,Ketones,Organic acids Get e-Alerts

Other Uses of Laboratory Automation: Statistically Designed Experiments in Organic Chemical Process Research and Development

Other Uses of Laboratory Automation: Statistically Designed Experiments in Organic Chemical Process Research and Development

Other Uses of Laboratory Automation: Statistically Designed Experiments in Organic Chemical Process Research and Development

Other Uses of Laboratory Automation: Statistically Designed Experiments in Organic Chemical Process Research and Development

The synthesis of oxazolines using the vilsmeier reagent

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTThe Synthesis of Oxazolines Using the Vilsmeier ReagentPeter G. M. Wuts, Jill M. Northuis, and Tricia A. KwanView Author Information Chemical Process Research and Development, 1500-91-201, Pharmacia and Upjohn, Kalamazoo, Michigan 49001 [email protected]Cite this: J. Org. Chem. 2000, 65, 26, 9223–9225Publication Date (Web):November 28, 2000Publication History Received3 July 2000Published online28 November 2000Published inissue 1 December 2000https://doi.org/10.1021/jo000664rCopyright © 2000 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1838Altmetric-Citations45LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (43 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Alcohols,Anions,Chemical reactions,Pyridines,Reagents Get e-Alerts

Automated Process Research. An Example of Accelerated Optimization of the Friedel−Crafts Acylation Reaction, a Key Step for the Synthesis of Anti-HIV (+)-Calanolide A

An automated process research approach to reaction optimization was developed. Chemical process research can be greatly accelerated by coupling automated synthesis equipment with statistical design of experiments (DoE). With the use of an automated process approach, multiple experiments can be performed in parallel on an automated platform, and multiple parameters that may influence process performance can be examined within one set of experiments generated from statistical design. We have successfully applied an automated process research approach to optimize the Friedel−Crafts acylation reaction that was used in our total synthesis of (+)-calanolide A, a potential anti-HIV agent currently in clinical trials. The in situ yield for a coumarin product was successfully optimized, increasing from 70% to 97% by HPLC analysis.

Cleavage of N ',N '-dialkylhydrazides with PhI(OH)OTs

N',N'-Dimethylhydrazides are efficiently cleaved to give the carboxylic acid upon treatment with PhI(OH)OTs in water or water/CH(2)Cl(2) mixtures. The reaction occurs with the evolution of a gas.

Chemical Process Synthesis of -Amino Acids and Esters

The importance of p-amino acids and esters for the synthesis of potential therapeutic agents and biologically active compounds is well known and the subject of this special issue. This review outlines some of the recent approaches reported for the synthesis of both racemic and enantiomeric p-amino acids and e ters with emphasis on those used for large scale production. This compilation is written from a chemical process perspective focusing on the practical application of these processes for large scale synthesis. A survey of procedures described in patent publications as well as current advances from chemical process research groups and results from our laboratory are included with emphasis on asymmetric Michael-type additions, addition of metal enolates to imines/sulfinimines, classical and enzymatic resolutions, and reduction of enantiomeric enamines.

Breaking the New Bottleneck: Automated Synthesis in Chemical Process Research and Development

An overview of the current methods, available systems, and applications of laboratory automation in chemical process research and development is given. Examples of the successful implementation of automated synthesis into reaction optimisation and process development are discussed.

Integrated Computing System of Laboratory Experiment for a Automation of Research Modeling and Design of Chemical Engineering Processes

Abstract The paper concerns integrated computing system with distributed data bases of laboratory experiment for automation of research, modeling and optimal design of chemical engineering processes. The computation methods of kinetic experiment for establishing the probable mechanism and composing kinetic models of complex reaction has been discussed The selection of accurate, single-valued and complete kinetic models allows to find theoretically optimum temperature distribution for substantiation of reactor type. Identification procedures of the mathematical models in static and dynamics of catalytic reactors have been suggested and the calculations of concentration and temperature fields were made on these bases stability conditions of stationary slates and transient processes have been determined.The packages of programmed modules permitting the realization of algorithms modeling and optimum calculation of catalytic processes in the framework of CAD in terms data base have been developed. The results that obtained from the mathematical models and optimum parameters and control design of new oxidation-dchydrogenation processes using this systems will be presented in the conclusion.

Effects of carbon dioxide variations in the unsaturated zone on water chemistry in a glacial-outwash aquifer

The research site at Otis Air Base, Cape Cod, Massachusetts, has been developed for hydrogeological and geochemical studies of sewage-effluent contaminated ground water since 1982. Research of hydrologic properties, transport, and chemical and biological processes is ongoing, but the origin of background water chemistry has not been determined. The principal geochemical process giving rise to the observed background water chemistry is CO 2-controlled hydrolysis of Na feldspar. Geochemical modeling demonstrated that CO 2 sources could vary over the project area. Analyses of unsaturated zone gases showed variations in CO 2 which were dependent on land use and vegetative cover in the area of groundwater recharge. Measurements of CO 2 in unsaturated-zone gases showed that concentrations of total inorganic C in recharge water should range from about 0.035 to 1.0 mmoles/L in the vicinity of Otis Air Base. Flux of CO 2 from the unsaturated zone varied for 4 principal land uses, ranging from 86 gC/m 2/yr for low vegetated areas to 1630 gC/m 2/yr for a golf course. Carbon dioxide flux from woodlands was 220 gC/m 2/yr, lower than reported fluxes of 500 to 600 gC/m 2/yr for woodlands in a similar climate. Carbon dioxide flux from grassy areas was 540 gC/m 2/yr, higher than reported fluxes of 230 to 490 gC/m 2/yr for grasslands in a similar climate.

Redox Titrants in Nonaqueous Media

I. INTRODUCTION Titrimetric methods based on redox reactions constitute at present one of the most extensive and most developed fields of analytical chemistry.1-4 Increased attention recently has been paid to redox titrations in nonaqueous or mixed media.5-7 Although systematic research of chemical processes in nonaqueous media began in the beginning of this century, it was originally concentrated almost exclusively on acid-base reactions. The theoretical treatment and practical use of redox reactions in nonaqueous media have not yet attained the level common for acid-base reactions. The main reason is that redox reactions are complex processes in which the actual electron transfer is only one of several steps. Especially with organic substances, the overall process involves dissociation and formation of covalent bonds that usually occurs in several steps with formation of variously reactive intermediates. For this reason, it is impossible to use the values of formal redox potentials for prediction of ana...

Kellogg's Chemical Process Research Makes Broad Demands on Analytical Section

Kellogg's Chemical Process Research Makes Broad Demands on Analytical Section