Search Results - "Otte, Douglas A."

Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes by Otte, Douglas A. L, Woerpel, K. A

“…Addition of allylmagnesium reagents to an aliphatic aldehyde bearing a radical clock gave only addition products and no evidence of ring-opened products that…”
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Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions by Garcia, Angie, Otte, Douglas A. L., Salamant, Walter A., Sanzone, Jillian R., Woerpel, K. A.

“…In contrast to observations with carbohydrates, experiments with 4‐alkoxy‐substituted acetals indicate that an alkoxy group can accelerate acetal hydrolysis by…”
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Influence of Alkoxy Groups on Rates of Acetal Hydrolysis and Tosylate Solvolysis: Electrostatic Stabilization of Developing Oxocarbenium Ion Intermediates and Neighboring-Group Participation To Form Oxonium Ions by Garcia, Angie, Otte, Douglas A. L, Salamant, Walter A, Sanzone, Jillian R, Woerpel, K. A

“…The hydrolysis of 4-alkoxy-substituted acetals was accelerated by about 20-fold compared to that of sterically comparable substrates that do not have an alkoxy…”
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Single-Molecule Imaging of Platinum Ligand Exchange Reaction Reveals Reactivity Distribution by Esfandiari, N. Melody, Wang, Yong, Bass, Jonathan Y, Cornell, Trevor P, Otte, Douglas A. L, Cheng, Ming H, Hemminger, John C, McIntire, Theresa M, Mandelshtam, Vladimir A, Blum, Suzanne A

“…Single-molecule fluorescence microscopy provided information about the real-time distribution of chemical reactivity on silicon oxide supports at the…”
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13C NMR Spectroscopy for the Quantitative Determination of Compound Ratios and Polymer End Groups by Otte, Douglas A. L, Borchmann, Dorothee E, Lin, Chin, Weck, Marcus, Woerpel, K. A

“…13C NMR spectroscopic integration employing short relaxation delays was evaluated as a quantitative tool to obtain ratios of diastereomers, regioisomers,…”
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Development of a Green and Sustainable Manufacturing Process for Gefapixant Citrate (MK-7264) Part 4: Formylation–Cyclization as a Flow–Batch Process Leads to Significant Improvements in Process Mass Intensity (PMI) and CO Generated versus the Batch–Batch Process by Otte, Douglas A. L, Basu, Kallol, Jellett, Lisa, Whittington, Michael, Spencer, Glenn, Burris, Matthew, Corcoran, Emily B, Stone, Kevin, Nappi, Jarod, Arvary, Rebecca A, Donoghue, David, Ren, Hong, Maloney, Kevin M, Naber, John R

“…Gefapixant citrate (MK-7264) is a P2X3 antagonist for the treatment of chronic cough. The second generation manufacturing route developed for the Step 3A/3B…”
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Development of a Green and Sustainable Manufacturing Process for Gefapixant Citrate (MK-7264) Part 1: Introduction and Process Overview by Ren, Hong, Maloney, Kevin M, Basu, Kallol, Di Maso, Michael J, Humphrey, Guy R, Peng, Feng, Desmond, Richard, Otte, Douglas A. L, Alwedi, Embarek, Liu, Wenjun, Zhang, Si-Wei, Song, Siqing, Arvary, Rebecca A, Zompa, Michael A, Lehnherr, Dan, Martin, Gary E, Chang, Hsieh Yao D, Mohan, Anne E, Guzman, Francisco J, Jellett, Lisa, Lee, Alfred Y, Spencer, Glenn, Fisher, Elizabeth S, Naber, John R, Gao, Hong, Lohani, Sachin, Ruck, Rebecca T, Campeau, Louis-Charles

“…A robust, green, and sustainable manufacturing process has been developed for the synthesis of gefapixant citrate, a P2X3 receptor antagonist that is under…”
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Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions by Garcia, Angie, Otte, Douglas A. L., Salamant, Walter A., Sanzone, Jillian R., Woerpel, K. A.

“…In contrast to observations with carbohydrates, experiments with 4‐alkoxy‐substituted acetals indicate that an alkoxy group can accelerate acetal hydrolysis by…”
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An Unusual, DDQ-Promoted Oxidative Rearrangement of 9,9-Disubstituted 1,4,5,8-Tetrahydro-4a,8a-methanonaphthalenes by Barasz, Jonah A, Ghaffari, Ali H, Otte, Douglas A, Thamattoor, Dasan M

“…The action of excess DDQ on 1,4,5,8-tetrahydro-4a,8a-methanonaphthalenes bearing a methyl group and one other substituent (cyclopropyl, methyl, phenyl) at the…”
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A new chemical tool for exploring the physiological function of the PDE2 isozyme by Chambers, Robert J., Abrams, Kristin, Garceau, Norman Y., Kamath, Ajith V., Manley, Christopher M., Lilley, Susan C., Otte, Douglas A., Scott, Dennis O., Sheils, Alissa L., Tess, David A., Vellekoop, A. Samuel, Zhang, Yan, Lam, Kelvin T.

“…Oxindole ( 2) is a potent and selective PDE2 inhibitor with a favorable ADME, physiochemical and pharmacokinetic profile to allow for use as a chemical tool in…”
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A Continuing Career in Physical Organic Chemistry: Donna G. Blackmond by Ji, Yining, Otte, Douglas A. L., Ruck, Rebecca T.

“…On the occasion of Professor Donna G. Blackmond’s winning of the 2023 James Flack Norris Award in Physical Organic Chemistry from the American Chemical…”
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Pilot-Scale Operation and Characterization of an Organolithium-Mediated Coupling Reaction in Flow to Form a Ketone Intermediate on the Route to Nemtabrutinib by Franklin, Robert D., Armiger, Travis, Otte, Douglas A. L., Larson, Reed T., Spencer, Glenn, Patel, Pratiq A., Paulines, Mellie June, Hall, Jackson R., Xiao, Kai-Jiong, Fier, Patrick S., Rodrigues, Vailankanni L., Guetschow, Erik D., Kuhl, Nadine, Jellett, Lisa, Corry, James, Chung, Cheol K., Thaisrivongs, David A.

“…In one of the two penultimate steps in the commercial route to nemtabrutinib, a ketone intermediate is formed from 7-bromo-6-chloro-7-deazapurine and methyl…”
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Development of a Green and Sustainable Manufacturing Process for a Key Intermediate to Nemtabrutinib (MK-1026): Sequential Deprotonation–Lithiation as a Batch–Flow Process by Otte, Douglas A. L., Larson, Reed T., Alwedi, Embarek, Armiger, Travis, Chen, Yonggang, Chung, Cheol K., Corry, James, Desmond, Richard, Fier, Patrick S., Franklin, Robert D., Guetschow, Erik D., Hall, Jackson R., Halsey, Holst M., Hartmanshenn, Clara, Jellett, Lisa, Kuhl, Nadine, Lévesque, François, McMullen, Jonathan P., Patel, Pratiq A., Paulines, Mellie June, Ren, Hong, Rodrigues, Vailankanni L., Ruccolo, Serge, Tan, Lushi, Thaisrivongs, David A., Xiao, Kai-Jiong

“…Nemtabrutinib (MK-1026) is a novel oral Bruton’s tyrosine kinase (BTK) inhibitor for treatment of B-cell cancers. An initial synthetic supply route to generate…”
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13 C NMR Spectroscopy for the Quantitative Determination of Compound Ratios and Polymer End Groups by Otte, Douglas A. L., Borchmann, Dorothee E., Lin, Chin, Weck, Marcus, Woerpel, K. A.

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New Perspectives: I. 13C NMR Spectroscopy for the Quantitative Determination of Compound Ratios; II. Evidence That Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes by Otte, Douglas A

“…The ability to predict the outcomes of experiments is an important skill for any scientist. To predict the outcomes of chemical reactions, one must first…”
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New Perspectives: I. 13C NMR Spectroscopy for the Quantitative Determination of Compound Ratios; II. Evidence That Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes by Otte, Douglas A

“…The ability to predict the outcomes of experiments is an important skill for any scientist. To predict the outcomes of chemical reactions, one must first…”
Get full text