Discovery of (R)-4-Benzyl-2-oxazolidinone

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Design and synthesis of an orally active macrocyclic neutral endopeptidase 24.11 inhibitor

A potent macrocyclic inhibitor of neutral endopeptidase (NEP) 24.11 was designed using a computer model of the active site of thermolysin. This 10- membered ring lactam represents a general mimic for any hydrophobic dipeptide in which the two amino acid side chains bind to an enzyme in a contiguous orientation. The parent 10-membered ring lactam was synthesized and exhibited excellent potency as an NEP 24.11 inhibitor (IC50 = 3 nM). In order to improve oral bioavailability, various functionality was attached to the macrocycle. These modifications lead to CGS 25155, an orally active NEP 24.11 inhibitor that slows down the degradation of the cardiac hormone atrial natriuretic factor, producing a lowering of blood pressure in the DOCA-salt rat model of hypertension.

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Extended knowledge of 497-25-6

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Synthesis of a radioactive photoaffinity arachidonic acid analog

A novel photoaffinity probe based of arachidonic acid was synthesized by coupling 20-hydroxyarachidonic acid and 2-azido-5-iodobenzoic acid. The key epoxide required for the formation of 20-hydroxyarachidonic acid was obtained using a new mild and safe method.

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1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position

The use of a 1,3,4-oxadiazole in combination with an 8-hydroxy-1,6-naphthyridine ring system has been shown to deliver potent enzyme and antiviral activity through inhibition of viral DNA integration. This report presents a detailed structure-activity investigation of the C5 position resulting in low nM potency for several analogs with an excellent therapeutic index.

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A new application about Oxazolidin-2-one

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Related Products of 497-25-6, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.497-25-6, Name is Oxazolidin-2-one, molecular formula is C3H5NO2. In a article£¬once mentioned of 497-25-6

Reactions of secondary propargylamines with heteroallenes for the synthesis of diverse heterocycles

This focused review aims to summarize recent developments in the processes involving additions of secondary propargylamines to various heteroallenes and subsequent transition metal-catalyzed or electrophile-mediated cyclizations. The utility of this convenient and tunable strategy spans from the carbon dioxide fixation and target-oriented synthesis of complex natural and biologically active products to the generation of extended synthetic libraries of diverse oxygen-, nitrogen- and sulfur-containing heterocycles. For comparative purposes, the analogous transformations of propargylic alcohols are also highlighted in this account.

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Some scientific research about (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

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A useful modification of the Evans auxiliary: 4-Isopropyl-5,5- diphenyloxazolidin-2-one

The 4-isopropyl-5,5-diphenyloxazolidinone (1) is readily prepared from (R)- or (S)-valine ester, PhMgBr, and ethyl chlorocarbonate. It has a melting point of ca. 250, a low solubility in most organic solvents, and a C=O group which is sterically protected from nucleophilic attack. Thus, the soluble N-acyl-oxazolidinones (7-16) can be prepared from 1 with BuLi at temperatures around 0instead of – 78(Scheme 3), their Li enolates can be generated with BuLi, rather than with LDA, and deacylation in the final step of the procedure can be achieved with NaOH at ambient temperatures (Scheme 12), with facile recovery of the precipitating auxiliary 1 (filtering, washing, and drying). The following reactions of N-acyl-oxazolidinones from 1 have been investigated: alkylations (Scheme 4), aminomethylations and hydroxymethylations (Scheme 5), aldol additions (Schemes 6 and 7), Michael additions (Schemes 9 and 10), and a (4 + 2) cycloaddition (Scheme 11). The well-known features of reactions following the Evans methodology (yield, diastereoselectivity, dependence on conditions, counter ions, additives etc.) prevail in these transformations. Most products, however, have higher melting points and a much more pronounced crystallization tendency than those derived from conventional oxazolidinones, and can thus be purified by recrystallization, avoiding chromatography (Table 1). The disadvantage of 1 having a higher molecular weight (ca. 150 Da) than the non-phenyl-substituted auxiliary is more than compensated by the ease of its application, especially on large scale. A number of crystal structures of oxazolidinones derived from 1 and a TiCl4 complex of an oxazolidinone are described and discussed in view of the diastereoselective-reaction mechanisms.

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The Absolute Best Science Experiment for (S)-4-Phenyl-3-propionyloxazolidin-2-one

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[…] intermediate and its preparation method and application (by machine translation)

The invention discloses […] intermediate and its preparation method and application. The […] intermediates have the following formula III and/or formula IV shown in chemical structure shown in chemical structure. Wherein R is phenyl, benzyl, isopropyl; the application of the invention intermediate synthesis […], the preparation process is simple, mild reaction conditions, environmental protection and the like. To realize the low-cost, large-scale, high efficiency for preparing high-purity […] has important significance and use value. (by machine translation)

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 95715-86-9, name is Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate, introducing its new discovery. SDS of cas: 95715-86-9

Improved synthesis of chiral N-protected allylic amines

The alpha-ester group of N-protected alpha-amino esters was reduced with diisobutylaluminum hydride to an intermediate aluminoxy acetal that on reaction with a Wittig reagent afforded the title chiral compounds in 48-78% chemical yields.

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The important role of 160695-26-1

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An Activated Germanium Metal-Promoted, Highly Diastereoselective Reformatsky Reaction

Activated germanium metal, prepared by the reduction of germanium(II) iodide with potassium metal, was found to promote the Reformatsky reaction effectively under mild conditions. In the presence of activated germanium metal, the reactions of alpha-bromo ketones 2a and 2b and alpha-bromo imides 2e and 2f with benzaldehyde (1a) proceeded smoothly to give the corresponding beta-hydroxy carbonyl compounds 3a, 3b, 3e and 3f, respectively, in good yields and with good syn diastereo- selectivity. The activated germanium metal-promoted, asymmetric Reformatsky reaction of enantiomerically pure-oxazolidinone derivatives 2g-j with various aldehydes 1a-d was also examined; the highest diastereoselectivity was achieved when (1S,2R)-2-amino-1,2-diphenylethanol- derived 2j was used as the Reformatsky donor. The excellent diastereoselectivity could be explained in terms of the formation of a chairlike, six-membered transition state between the aldehyde and enolate as in the Zimmerman-Traxler model. A single recrystallization of the Reformatsky adducts, followed by hydrolysis and subsequent esterification, led to enantiomerically pure methyl 3-hydroxy- 2-methylalkanoates 10j-m, with almost quantitative recovery of the enantiomerically pure 2-oxazolidinone 14.

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Process for the preparation of polyalkylphenoxyaminoalkanes

A process for the preparation of polyalkylphenoxyaminoalkanes which comprises the aminoethylation of a polyalkylphenol compound in the presence of a basic catalyst with 2-oxazolidinone or a derivative thereof having the following formula: wherein R1 and R2 are independently hydrogen or lower alkyl having 1 to about 6 carbon atoms and wherein the polyalkyl group of said polyalkylphenol has an average molecular weight in the range of about 600 to 5,000.

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PROCESS FOR A CETP INHIBITOR

An efficient process is disclosed for producing the compound of formula I, which is the CETP inhibitor anacetrapib, which raises HDL-cholesterol and reduces LDL-cholesterol in human patients and may be effective for treating or reducing the risk of developing atherosclerosis:.

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