Discovery of (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one

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The (S) alcohol in the benzylic position of compound 2, a key intermediate in the synthesis of the cholesterol lowering agent Ezetimibe, was introduced by the (R)-MeCBS catalyzed asymmetric carbonyl reduction of ketone 1 using borane diethylaniline complex (BDEA) as the reducing agent. The latter was prepared in situ from sodium borohydride (NaBH4), diethylaniline (DEA) and dimethylsulfate (DMSO4). BDEA prepared in situ offers considerable advantages from the industrialization standpoint (cost and stability on storage of the reagents) over commercial solutions of BH3-THF (BTHF) or BH3-DMS (BMS). The effect of critical reaction parameters such as addition mode of reagent, temperature, solvent, reaction quenching as well as LiCl addition on the selectivity has been examined. This reaction has been successfully applied in the process for the preparation of key intermediate 2 for Ezetimibe.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2851NO – PubChem

 

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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, 189028-95-3, name is (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one, introducing its new discovery. Application In Synthesis of (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one

Process for the preparation of 1,3,2-oxazaborolidine compounds

A process is used for the preparation of 1,3,2-oxazaborolidine compounds. This process prepares compounds of formula (I) or (IA): in which: R1 is an alkyl or an aryl; and R2, R3, R4 and R5 are especially a hydrogen atom or an alkyl, wherein the following are reacted in two steps: a) a boric precursor compound with an acetal compound to give a boronate compound; and b) the boronate compound with an amino alcohol compound. This process avoids by-products and exhibits a very good stereospecificity.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2822NO – PubChem

 

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PROCESS FOR ASYMMETRIC SYNTHESIS OF HYDROXY-ALKYL SUBSTITUTED AZETIDINONE DERIVATIVES OF INTERMEDIATES THEREOF

Provided herein are processes for asymmetric synthesis of hydroxyalkyl-substituted azetidinone derivatives or intermediates thereof via stereoselective reduction of benzylic ketone using (-)-B-chlorodiisopinocampheylborane. Also provided herein are processes for preparing ezetimibe.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2831NO – PubChem

 

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Anti-hypercholesterolemic biaryl azetidinone compounds

This invention provides cholesterol absorption inhibitors of Formula I: and the pharmaceutically acceptable salts thereof, wherein R12 is an alkyl, alkeny or alkynyl group mono- or poly-substituted with -OH, -COOH or a combination of -OH and -COOH, and R9 contains an alkyl, alkeny or alkynyl group substituted with a heterocyclic ring, amino or sulfonyl. The compounds are useful for lowering plasma cholesterol levels, particularly LDL cholesterol, and for treating atherosclerosis and preventing atherosclerotic disease events.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2826NO – PubChem

 

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One method for synthesizing intermediate folds Mai Bu (by machine translation)

The invention discloses a method for the synthesis of the intermediates folds Mai Bu , the synthesis method with compound I as the raw material, the compound is mixed with the reaction solution I, fu Suanji and under the action of the, compound I is first extra valeryl chlorine activation, then and S-4-phenyl-2-oxazolidine alkone coupling , the (R)-2-methyl-CBS-oxazole borane reduction reaction, after-treatment is the (4S)-3-[ (5S)-5-(4-fluoro phenyl)-5-hydroxy- fifth heavenly stem acyl group ]-4-phenyl -1, 3-oxygen nitrogen heterocyclic pentane-2-one (II); Wherein the reaction solution comprises tetrahydrofuran, chloroform, dioxane or dichloromethane. The invention discloses one method for synthesizing intermediate folds Mai Bu has the advantages of simple operation, the synthetic route is short, the advantages of synthetic low cost, is suitable for large-scale industrial production. (by machine translation)

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2847NO – PubChem

 

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, category: oxazolidine, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 189028-95-3, Name is (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one, molecular formula is C20H20FNO4

Process For Production Of 4-Biphenylyazetidin-2-Ones

The present invention relates to processes for the production of 4-biphenylylazetidin-2-one derivatives of formula

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2837NO – PubChem

 

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METHOD OF PRODUCING OPTICALLY ACTIVE ALCOHOL

This invention relates to a process for producing optically active alcohols using asymmetric reduction of aromatic ketones. This process gives optically active alcohols in high enantioselectivity at large scale production. Aromatic ketones represented by formula (I) [wherein, R1 are selected from hydrogen atom, halogen atom, lower alkyl group etc. R2 is -(CH2)n-R3 [wherein, n is 1 to 5 integer. R3 are selected from hydrogen atom, halogen atom, lower alkoxycarbonyl group etc. and formula (II) and (III). {wherein, R4 is selected from lower alkyl group (1 to 5 carbon atom) etc. R5 and R6 are the same or different and are selected from hydrogen atom, halogen atom, lower alkyl group etc.}]] are reduced by sodium borohydride, chlorotrimethylsilane and optically active 2-[bis(4-methoxyphenyl)hydroxymethyl]pyrrolidine represented by formula (IV) to give optically active alcohol represented by formula (V) stereoselectively. (wherein, R1 and R2 are as defined above.)

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2841NO – PubChem

 

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Application In Synthesis of (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 189028-95-3, name is (S)-3-((S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one. In an article,Which mentioned a new discovery about 189028-95-3

A new class of according to booklet mai bu analogue and its preparation method (by machine translation)

The present invention provides a new class of according to booklet mai bu analogs, its structural formula shown in formula I: The invention according to booklet of the mai bu analogs according to booklet mai bu improves the water-soluble, more conducive to clinical use. (by machine translation)

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2842NO – PubChem

 

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Related Products of 189028-95-3, 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, 189028-95-3, molcular formula is C20H20FNO4, introducing its new discovery.

Crystal form of ezetimibe key intermediate and preparation method thereof (by machine translation)

The invention discloses a crystal form of a ezetimibe key intermediate and a preparation method. The invention relates to (4S) -3 – [(5S) -5 – (4 – fluorophenyl) -5 – hydroxyvaleryl] -4 – phenyl -2 – oxazolidinone crystal form and a preparation method. In particular, the present invention provides a crystalline form, of a compound of formula (I), having an X-ray powder diffraction pattern at 2 theta, characterized by a characteristic diffraction peak: 6.195 ±0.2 , 7.640 ±0.2 , 8.289 ±0.2 , 12.847 ±0.2 , respectively. 18.394 ±0.2 , 19.871 ±0.2 , 21.548 ±0.2 , 25.062 ±0.2 . (by machine translation)

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2839NO – PubChem

 

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Biocatalysis as useful tool in asymmetric synthesis: An assessment of recently granted patents(2014-2019)

The broad interdisciplinary nature of biocatalysis fosters innovation, as different technical fields are interconnected and synergized. A way to depict that innovation is by conducting a survey on patent activities. This paper analyses the intellectual property activities of the last five years (2014-2019) with a specific focus on biocatalysis applied to asymmetric synthesis. Furthermore, to reflect the inventive and innovative steps, only patents that were granted during that period are considered. Patent searches using several keywords (e.g., enzyme names) have been conducted by using several patent engine servers (e.g., Espacenet, SciFinder, Google Patents), with focus on granted patents during the period 2014-2019. Around 200 granted patents have been identified, covering all enzyme types. The inventive pattern focuses on the protection of novel protein sequences, as well as on new substrates. In some other cases, combined processes, multi-step enzymatic reactions, as well as process conditions are the innovative basis. Both industries and academic groups are active in patenting. As a conclusion of this survey, we can assert that biocatalysis is increasingly recognized as a useful tool for asymmetric synthesis and being considered as an innovative option to build IP and protect synthetic routes.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2853NO – PubChem