A5051705804- Synthetic Organic Chemistry Methods
- Asymmetric Synthesis and Catalysis
- Chemical Synthesis and Analysis
- Synthesis and Biological Evaluation
- Fluorine in Organic Chemistry
- Synthesis and Reactions of Organic Compounds
- Chemical Synthesis and Reactions
- Organic Chemistry Cycloaddition Reactions
- Carbohydrate Chemistry and Synthesis
- Organic Chemistry Synthesis Methods
- Marine Sponges and Natural Products
- Asymmetric Hydrogenation and Catalysis
- Water Treatment and Disinfection
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- HIV/AIDS drug development and treatment
- Synthesis and Catalytic Reactions
- Quinazolinone synthesis and applications
- Radical Photochemical Reactions
- Enzyme Catalysis and Immobilization
- Catalytic Alkyne Reactions
- Traditional and Medicinal Uses of Annonaceae
- Organometallic Complex Synthesis and Catalysis
- Click Chemistry and Applications
- Steroid Chemistry and Biochemistry
Vertex Pharmaceuticals (United States)
2011-2023
Pfizer (United States)
2002-2013
Hormel (United States)
1996-1998
Purdue University West Lafayette
1991
Ball State University
1986
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTInverse electron-demand Diels-Alder reactions of N-sulfonyl .alpha.,.beta.-unsaturated imines: a general approach to implementation the 4.pi. participation 1-aza-1,3-butadienes in reactionsDale L. Boger, Wendy Corbett, Timothy T. Curran, and A. M. KasperCite this: J. Am. Chem. Soc. 1991, 113, 5, 1713–1729Publication Date (Print):February 1, 1991Publication History Published online1 May 2002Published inissue 1 February...
Most secondary amines have the potential to undergo nitrosation in presence of nitrite under certain conditions, particularly at low pH, generate N-nitrosamines. Tertiary are generally considered be less prone nitrosamine formation as they require an additional dealkylation step. A review published literature combined with recently generated experimental data from experiments carried out on several trialkyl further informs extent that tertiary can form N-nitrosamines by reaction trace levels...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDiels-Alder reactions of 1-aza-1,3-butadienes: room temperature, endo-selective LUMOdiene-controlled [4 + 2] cycloaddition N-sulfonyl-4-(ethoxycarbonyl)-1-aza-1,3-butadienesDale L. Boger and Timothy T. CurranCite this: J. Org. Chem. 1990, 55, 20, 5439–5442Publication Date (Print):September 1, 1990Publication History Published online1 May 2002Published inissue 1 September...
Novel 5-(1'-hydroxy)-γ-butyrolactone and γ-butyrolactam subunits were synthesized by direct vinylogous aldol addition of α,β-dichloro γ-butyrolactones γ-butyrolactams with aldehydes under basic conditions. Different bases solvents screened in the context generating γ-butyrolactones. Diastereoselectivity was observed γ-butenolides showed opposite diastereoselectivity same reaction condition.
Drug recalls have led to increased regulatory scrutiny into the formation and presence of nitrosamine (N-nitrosoamine) impurities in medicines. This review aims assist development risk mitigation strategies by summarizing known reactions nitrosamines, with a focus on useful within context complex molecule synthesis. should serve as reference help lead chemical processes which effectively control nitrosamines.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of the lower subunit rhizoxinDale L. Boger and Timothy T. CurranCite this: J. Org. Chem. 1992, 57, 8, 2235–2244Publication Date (Print):April 1, 1992Publication History Published online1 May 2002Published inissue 1 April 1992https://pubs.acs.org/doi/10.1021/jo00034a010https://doi.org/10.1021/jo00034a010research-articleACS PublicationsRequest reuse permissionsArticle Views840Altmetric-Citations43LEARN ABOUT THESE METRICSArticle Views are...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPreparation of .alpha.,.alpha.-difluoro-.beta.-hydroxy esters via a modified Reformatsky reactionTimothy T. CurranCite this: J. Org. Chem. 1993, 58, 23, 6360–6363Publication Date (Print):November 1, 1993Publication History Published online1 May 2002Published inissue 1 November 1993https://pubs.acs.org/doi/10.1021/jo00075a033https://doi.org/10.1021/jo00075a033research-articleACS PublicationsRequest reuse permissionsArticle...
This paper describes the synthesis of two amino-quinazolinediones which are potent gyrase/topoisomerase inhibitors and useful as antibacterial agents. The early scale-up work to prepare a chiral side chain on multigram scale different amino-quinazolinedione cores is detailed. enabling for employed previously reported Michael addition MeNO2 an enantiomerically enriched δ-amino-enoate two-step de-oxygenation lactam. Key synthetic steps core preparation completion include dianion-promoted...
The risk assessment and control of N-nitrosamine impurities in medicines is a topic great concern for patients, regulators, the pharmaceutical industry. This paper discusses modeling approach to predict solvent–water partition coefficient 28 N-nitrosamines 134 water immiscible solvents, including those solvents typically used manufacturing. Conductor-like Screening Model Real Solvents model has been because its implementation from first principles does not require regressing specific...
The preparation of a few (nitrophenyl)hydroxylamines and reaction with two quinazoline-2,4-diones is described. electrophilic aminating agents were assessed in terms yield for the N-amination safety considerations rapid scale-up. For amination described system, best highest onset temperature found same agent, specifically, (4-nitrophenyl)hydroxylamine.
Lewis acid catalyzed addition of active methylene compounds to mucochloric (1) and mucobromic (2) affording Knoevenagel aldol adducts, gamma-substituted gamma-butenolides, has been explored. Catalytic efficiencies various acids have compared. Indium acetate (0.25-5 mol %) was found be the most efficient catalyst.
Abstract Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated (warming shining light) in an open container. A subsequent fragmentation resulted formation the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic β-hydroxy-propionamides absence a radical promoter has not reported.
(S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile (1) is a key intermediate in the preparation of PF-00951966, fluoroquinolone antibiotic for use against pathogens causing community-acquired respiratory tract infections including multidrug resistant (MDR) organisms. The current work describes development highly efficient and stereoselective synthesis 1 10 steps with an overall yield 24% from readily available benzyloxyacetyl chloride. Two transformations synthetic sequence involve...
This account documents our recent progress in exposing some of the potential mucohalic acids synthetic applications. Understanding their stability and reactivity different reaction media allows development mild regioselective methods to access various substituted butenolides, butenolactams, 4,5-dihalopyridazin-3(2<i>H</i>)-ones create other novel, multifunctionalized building blocks. 1 Introduction 2 The Rationale for Reinvestigation Mucohalic Acid Chemistry 3 Stability Acids 4 One-Pot...
The scale-up of a prototype HCV protease inhibitor (1) from gram scale in the laboratory to kilogram pilot plant is described. Key features optimization included synthesis bulk quantities exomethylene proline intermediate 6, separation diastereomers spirocycle 2 without chromatography, isolation precursor 1 purge byproducts that might raise genotoxic structural alerts, and purification an amorphous drug substance via crystalline acetic acid solvate.
An efficient synthesis of (1S,4R)-(−)-4-tert-butyldimethylsilyloxy-2-cyclopentenyl acetate and (1R,4S)-(−)-4-tert-butyldimethylsilyloxy-2-cyclopentenol is described utilizing a furfuryl alcohol rearrangement, followed by lithium aluminum hydride reduction with high facial selectivity an enzymatic resolution pancreatin. Both these intermediates were successfully utilized in the preparation carbocyclic nucleoside 9N-[(1'R,3'R)-trans-3'-hydroxycyclopentanyl]adenine hydrochloride, agent which...
Development work toward an enabling synthesis of preparative scale batches imidazole-based HMG-CoA reductase inhibitor is described. The desired target was synthesized in 16% yield over 7 steps, highlighted by imidazole-forming condensation reaction which the improved from 20% to >70% via modification solvent, acid, and amine equivalents. step 2 acylation improved, a problematic benzyl ester 4 converted into corresponding amide decrease trans-amidation during 5 imidazole formation. A highly...