Journal Article10.1039/B212454H
Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2- and 5-ones, and application to the synthesis of (R)-salmeterol.
44
TL;DR: A convenient and efficient method for the cleavage of 1,3-oxazolidin-5-ones and 1,2-oxAZolidin -2-ones utilising potassium trimethylsilanolate in tetrahydrofuran using the 2-oxzolidinone ring as a protecting group for the ethanolamine moiety is described.
read more
Abstract: A convenient and efficient method for the cleavage of 1,3-oxazolidin-5-ones and 1,3-oxazolidin-2-ones utilising potassium trimethylsilanolate in tetrahydrofuran is described. The benzyloxycarbonyl-protecting group is readily removed under the reaction conditions, whereas the N-benzoyl group is stable. A synthesis of (R)-salmeterol exploiting the 2-oxazolidinone ring as a protecting group for the ethanolamine moiety is also described.
read more
Chat with Paper
AI Agents for this Paper
Find similar papers on Google Scholar, PubMed and Arxiv
Write a critical review of this paper
Analyze citations of this paper to find unaddressed research gaps
Citations
Synthesis and Structure—Activity Relationships of Long-acting β2 Adrenergic Receptor Agonists Incorporating Metabolic Inactivation: An Antedrug Approach
Panayiotis A. Procopiou,Victoria J. Barrett,Nicola Bevan,Keith Biggadike,Philip Charles Box,Peter R. Butchers,Diane Mary Coe,Richard Conroy,Amanda Emmons,Alison J. Ford,Duncan S. Holmes,Helen Tracey Horsley,Fern Kerr,Anne-Marie Li-Kwai-Cheung,Brian Edgar Looker,Inderjit Singh Mann,Iain Mcfarlane Mclay,Valerie S. Morrison,Peter J. Mutch,Claire E. Smith,Paula Tomlin +20 more
TL;DR: Compound 13f had high potency, selectivity, fast onset, and long duration of action in vitro and was found to have long duration in vivo, low oral bioavailability in the rat, and to be rapidly metabolized.
102
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
Huan-Chieh Chien,Claire Colas,Karissa Finke,Seth Springer,Laura Stoner,Arik A. Zur,Brooklynn Venteicher,Jerome Campbell,Colton Hall,Andrew Flint,Evan Augustyn,Christopher Hernandez,Nathan Heeren,Logan Hansen,Abby Anthony,Justine Bauer,Dimitrios Fotiadis,Avner Schlessinger,Kathleen M. Giacomini,Allen A. Thomas +19 more
TL;DR: Surprisingly, LAT1 can transport amino acid-like substrates with wide-ranging polarities including those containing ionizable substituents and the rate of LAT1 transport was generally nonstereoselective even though enantiomers likely exhibit different binding modes.
Biaryl-Bridged Macrocyclic Peptides: Conformational Constraint via Carbogenic Fusion of Natural Amino Acid Side Chains
Falco-Magnus Meyer,James C. Collins,Brendan Borin,James Bradow,Spiros Liras,Chris Limberakis,Alan M. Mathiowetz,Laurence Philippe,David Price,Kun Song,Keith James +10 more
TL;DR: This approach constitutes a means of constraining peptide conformation via direct carbogenic fusion of side chains of naturally occurring amino acids such as phenylalanine and tyrosine, and so is complementary to strategies involving non-natural, for example, hydrocarbon, bridges.
58
Synthesis and structure-activity relationships of long-acting beta2 adrenergic receptor agonists incorporating arylsulfonamide groups.
Panayiotis A. Procopiou,Victoria J. Barrett,Nicola Bevan,Keith Biggadike,Peter R. Butchers,Diane M. Coe,Richard Conroy,Edney Dean David,Rita Field,Alison J. Ford,Stephen Barry Guntrip,Brian Edgar Looker,Iain M. McLay,Michael John Monteith,Valerie S. Morrison,Peter J. Mutch,Stephen A. Richards,Rosemary Sasse,Claire E. Smith +18 more
TL;DR: Sulfonamide 29b had the best profile of potency, selectivity, onset, andduration of action on both guinea pig trachea and human bronchus and was found to have low oral bioavailability in rat and dog and also to have long duration of action in an in vivo model of bronchodilation.
44
References
Metal silanolates: organic soluble equivalents for O−2
E.D. Laganis,B.L. Chenard +1 more
TL;DR: Alkali metal trimethylsilanolates, M⊕⊖OSiMe3, convert carboxylic acid derivatives into their corresponding anhydrous acid salts under mild non-aqueous conditions as mentioned in this paper.
213
N,O-acetals from pivalaldehyde and amino acids for the α-alkylation with self-reproduction of the center of chirality: enolates of 3-benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones
Dieter Seebach,Antoine Fadel +1 more
TL;DR: In this article, the oxazolidinones were deprotonated with lithium diethylamide (LDEA) in tetrahydrofuran (THF) and alkylated (Mel, benzyl bromide) or hydroxyalkylated (benzaldehyde).
151