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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.37675-18-6. In my other articles, you can also check out more blogs about 37675-18-6

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This article presents a stereospecific scale-up synthesis of (S)-1-((S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylic acid (BMS-960), a potent and selective isoxazole-containing S1P1 receptor agonist. The process highlights an enzymatic reduction of alpha-bromoketone toward the preparation of (S)-bromo alcohol, a key precursor of (S)-4-(oxiran-2-yl)benzonitrile. A regioselective and stereospecific epoxide ring-opening reaction was also optimized along with improvements to 1,2,4-oxadiazole formation, hydrolysis, and crystallization. The improved process was utilized to synthesize batches of BMS-960 for Ames testing and other toxicological studies.

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Piperidine – Wikipedia,
Piperidine | C5H8913N – PubChem

 

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Electric Literature of 37675-18-6, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.37675-18-6, Name is (S)-Ethyl piperidine-3-carboxylate, molecular formula is C8H15NO2. In a Article,once mentioned of 37675-18-6

An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764 was achieved. The key intermediate, an optically active ethynyl beta-amino ester, was synthesized efficiently by utilizing a lipase catalyzed kinetic resolution step.

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The construction of a library of benzothiaoxazepine-1,1?-dioxides utilizing a one-pot, SNAr diversification-ODCT50 scavenging protocol is reported. This protocol combines microwave irradiation to facilitate the reaction, in conjunction with a soluble ROMP-derived scavenger (ODCT) to afford the desired products in good overall purity. Utilizing this protocol, a 78-member library was successfully synthesized and submitted for biological evaluation.

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The history of peptide chemistry in our group is described. It all started with the cyclic undecapeptide cyclosporin, the immunosuppressive compound, which is commercialised as Sandimmune/Neoral by Sandoz/Novartis, and which has revolutionized transplant medicine. The discovery that cyclosporin can be deprotonated to a hexalithio derivative, and thus C-alkylated on a sarcosine moiety, led us into a research project on peptide modifications. We defined structural prerequisites for the use of peptide enolates and for electrolytic decarboxylation of peptides. Parallel to these activities, the group was engaged in developing synthetic methodologies aimed at stereoselective preparations of alpha-, beta-, and gamma-amino acid derivatives (cf. diastereoselective alkylations, self regeneration of stereogenic centers, axially chiral enolates). A third avenue into peptide chemistry originated from our investigations on the biopolymer PHB (poly-3-hydroxybutanoic acid); the question arose ‘what happens upon replacement of chain-bound O by NH in the polyester?’ A brief summary is given of the results obtained in our ensuing discovery tour of beta-peptides built of homologated proteinogenic amino acids. They form secondary structures with short chain lengths and they have unexpected physiological properties, rendering them candidates for peptidic drugs. The synthesis of beta3-peptides is straightforward, and in the meantime most of the Fmoc-protected building blocks are commercial. The beta2-homoamino acids are less readily available. Their preparation and the assembly of a beta2- eicosapeptide with the twenty proteinogenic side chains are discussed herein. The reasons for the chosen sequence and the strategy of what turned out to be a 159-step synthesis are described. Full experimental details are given for the preparation of the dimeric Fmoc-beta2hXaa(PG)- beta2hXaa(PG)-OH building blocks used, for their solid-phase coupling to two beta2-decapeptide segments, for the thioligation, and for the purification, isolation and spectroscopic characterization of the resulting 20mer. An outlook to future projects in the exciting field of beta- and gamma-peptide chemistry and biology is given.

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Piperidine – Wikipedia,
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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 37675-18-6, molcular formula is C8H15NO2, introducing its new discovery. Application In Synthesis of (S)-Ethyl piperidine-3-carboxylate

Sphingosine-1-phosphate (S1P) is a bioactive sphingolipid metabolite that regulates a multitude of physiological processes such as lymphocyte trafficking, cardiac function, vascular development, and inflammation. Because of the ability of S1P1 receptor agonists to suppress lymphocyte egress, they have great potential as therapeutic agents in a variety of autoimmune diseases. In this article, the discovery of selective, direct acting S1P1 agonists utilizing an ethanolamine scaffold containing a terminal carboxylic acid is described. Potent S1P1 agonists such as compounds 18a and 19a which have greater than 1000-fold selectivity over S1P3 are described. These compounds efficiently reduce blood lymphocyte counts in rats through 24 h after single doses of 1 and 0.3 mpk, respectively. Pharmacodynamic properties of both compounds are discussed. Compound 19a was further studied in two preclinical models of disease, exhibiting good efficacy in both the rat adjuvant arthritis model (AA) and the mouse experimental autoimmune encephalomyelitis model (EAE).

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SPHINGOSINE-1-PHOSPHATE RECEPTOR AGONISTS

Disclosed are compounds of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein: A is formula (II) Q is a substituted 5-membered monocyclic heteroaryl group; W is CH2, O, or NH; and R1, R2, R3, R4, R5, R6, m, n, t, and x are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

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Reference Example 5 To a mixture of (S)-ethyl nipecotate (1.15 g) and tetrahydrofuran (16 ml) was added lithium aluminum hydride (278 mg) at 0C. The mixture was stirred for 3 hours with elevating the temperature to room temperature. Water (0.28 ml), 25% potassium hydroxide solution (0.28 ml) and water (0.84 ml) were added thereto in this order, and the mixture was stirred for 15 hours. The insolubles were filtered off using celite and the mother liquor was concentrated, to give (S)-3-(hydroxymethyl)piperidine (797 mg). [alpha]D = -11.3 (c = 0.730, MeOH). 1H-NMR (300 Hz, CDCl3) delta: 1.07-1.20 (1H, m), 1.40-1.54 (1H, m), 1.61-1.82 (3H, m), 2.39 (1H, dd, J=12.0 and 9.9 Hz), 2.54-2.62 (3H, m), 2.95-3.01 (1H, m), 3.13-3.18 (1H, m), 3.40-3.54 (2H, m).

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Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1553074; (2005); A1;,
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[1495] LAH (118 mL, 1.0 M in Et2O, 1.0 eq.) was added to a solution of the product from Step A (18.5 g, 0.125 mmol) in THF (250 mL) at 0 C. over 20 minutes. The resulting solution was warmed slowly to room temperature and then heated at reflux 2 hours. The reaction was cooled to room temperature and quenched by the slow addition of saturated Na2SO4. The resulting slurry was dried by the addition of Na2SO4, filtered through Celite and concentrated to give a colorless oil (13.7 g, 98% crude yield). CIMS: MH+=116; [alpha]20D=-8.4 (5.0 mg in 2 mL MeOH).

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Reference£º
Patent; Zhu, Hugh Y.; Njoroge, F. George; Cooper, Alan B.; Guzi, Timothy; Rane, Dinanath F.; Minor, Keith P.; Doll, Ronald J.; Girijavallabhan, Viyyoor M.; Santhanam, Bama; Pinto, Patrick A.; Vibulbhan, Bancha; Keertikar, Kartik M.; Alvarez, Carmen S.; Baldwin, John J.; Li, Ge; Huang, Chia-Yu; James, Ray A.; Bishop, W. Robert; Wang, James J-S; Desai, Jagdish A.; US2003/229099; (2003); A1;,
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4.3.40 Ethyl (S)-1-(ethoxymethyl)piperidine-3-carboxylate, (S)-10 K2CO3 (2.8?g, 20?mmol) was added to a solution of ethyl nipecotate (3.2?mL, 20?mmol) in EtOH (7.0?mL, 0.12?mol) at 0?C. After 15?min paraformaldehyde (PFA) (0.63?g, 20?mmol) was added, and the mixture was stirred at 25?C for 6?h. The mixture was diluted with Et2O and filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by distillation (Kugelrohr distillation) at 130?C (0.4?Torr) to obtain the product N,O-acetal (rac-10) as a colorless oil (3.1?g, 71%). Analytical data corresponds to those of rac-10 except [alpha]D 20 = +13.3 (c?=?2.0, DCM).

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Reference£º
Article; Toth, Krisztian; Hoefner, Georg; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 26; 22; (2018); p. 5944 – 5961;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem