183905-31-9Relevant articles and documents
Diol-Ritter Reaction: Regio- And Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation
Abboud, Khalil A.,Cheng, Kevin,Klosin, Jerzy,Kruper, William J.,Kruper, William R.,Lysenko, Ivan,Ondari, Mark E.,Thomas, Pulikkottil J.
, (2021/10/20)
The well-known epoxide-Ritter reaction generally affords oxazolines with poor to average regioselectivity. Herein, a mechanism-based study of the less known diol-Ritter reaction has provided a highly regioselective procedure for the synthesis of 1-vic-amido-2-esters from either terminal epoxides or 1,2-diols via Lewis acid-catalyzed monoesterification. When treated with a stoichiometric Lewis acid catalyst (BF3), these diol monoesters form dioxonium cation intermediates that are ring-opened with nitrile nucleophiles to form nitrilium intermediates, which undergo rapid and irreversible hydration to give the desired amidoesters. Diester byproduct formation is irreversible and appears to occur through disproportionation of diol monoester. With chiral epoxide starting materials, the formation of amidoester occurs with retention of configuration and no apparent erosion of optical purity as determined by single-crystal X-ray analyses and chiral chromatography, respectively. The direct access to chiral vic-amidoesters is especially practical with regard to the synthesis of antibacterial oxazolidinone analogues of the Zyvox antimicrobial family.
Environment-friendly synthesis method of linezolid and intermediate thereof
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Paragraph 0043; 0044; 0045, (2018/11/22)
The invention relates to a more environment-friendly synthesis method of linezolid and a key intermediate thereof. The more environment-friendly synthesis method is characterized in that the key intermediate of linezolid is prepared through the steps of hydroxyl protection, carboxyl reduction, hydroxyl halogenation, ring closing, halogenation after hydroxyl deprotection, ring opening and the likeby taking a natural chiral product L-serine as an initial raw material. According to the more environment-friendly synthesis method provided by the invention, a chiral center is introduced by adoptingthe natural chiral product, the reaction yield is high, the technological operation is simple, the product purity is high, and the synthesis method is more environment-friendly and is suitable for industrial production.
the advantage cuts down Sha Ban and intermediate preparation method
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Paragraph 0074; 0080; 0081, (2017/07/31)
The present invention discloses a new method for preparing rivaroxaban through an intermediate represented by a formula (5), wherein the method comprises that: S-1-amino-3-chloro-2-propanol represented by a formula (2) is subjected to acylation modification to obtain a compound represented by a formula (3), the compound represented by the formula (3) reacts with 4-(3-oxomorpholineone)phenylamine formyl benzyl ester represented by a formula (4) under alkali catalysis so as to provide a structure represented by a formula (5) in a high yield manner, the intermediate is subjected to acid hydrolysis to prepare 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl-morpholin-3-one represented by a formula (6), and the 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl-morpholin-3-one reacts with 5-chlorothiophene-2-carbonyl chloride represented by a formula (c) to prepare the rivaroxaban. The rivaroxaban preparation method has advantages of high reaction yield, easy purification, mild reaction conditions, simple operation and the like, wherein the yield is significantly increased although acylation modification is required during the synthesis process, the purification process can be simplified, and the preparation method is suitable for industrial production.
OXAZOLIDINONE COMPOUNDS AND METHODS OF USE THEREOF AS ANTIBACTERIAL AGENTS
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Page/Page column 46; 47, (2017/05/19)
The present invention relates to oxazolidinone compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, E, and R1 are as defined herein. The present invention also relates to compositions which comprise at least one oxazolidinone compound of the invention. The invention also provides methods for inhibiting growth of mycobacterial cells as well as a method of treating mycobacterial infections by Mycobacterium tuberculosiscomprising administering a therapeutically effective amount of an oxazolidinone of the invention and/or apharmaceutically acceptable salt thereof, or a composition comprising such compound and/or salt.
PROCESS FOR THE PREPARATION OF (5S)-N-{3-[3,5-DIFLUORO-4-(4-HYDROXY-4-METHOXYMETHYL-PIPERIDIN-1-YL)-PHENYL]-2-OXO-OXAZOLIDIN-5-YLMETHYL}-ACETAMIDE
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Paragraph 10, (2016/02/16)
A process for preparation of compound of Formula (I) is provided.
OXAZOLIDINONE COMPOUNDS AND THEIR USES IN PREPARATION OF ANTIBIOTICS
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Paragraph 0065; 0066; 0067; 0068, (2014/06/24)
The invention belongs to the field of medicaments, and particularly relates to oxazolidinone compounds and their uses in the preparation of antibiotics. A technical problem to be solved by the invention is to provide new oxazolidinone compounds having the structure represented by Formula I. The oxazolidinone compounds of the invention, which are new compounds obtained through numerous screening, have significant antibacterial activity against bacteria such as drug-resistant staphylococcus aureus, fecal coliform bacteria, and streptococcus pneumoniae, while exhibiting low toxicity. The invention provides new options for the development and application of antibiotics.
Oxazolidinone Compounds and Their Uses in Preparation of Antibiotics
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Paragraph 0179; 0180; 0181; 0182, (2014/05/25)
The invention belongs to the field of medicaments, and particularly relates to oxazolidinone compounds and their uses in the preparation of antibiotics. A technical problem to be solved by the invention is to provide new oxazolidinone compounds having the structure represented by Formula I. The oxazolidinone compounds of the invention, which are new compounds obtained through numerous screening, have significant antibacterial activity against bacteria such as drug-resistant staphylococcus aureus, fecal coliform bacteria, and streptococcus pneumoniae, while exhibiting low toxicity. The invention provides new options for the development and application of antibiotics.
PREPARATION AND UTILITY OF SUBSTITUTED OXZOLIDINONES
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Page/Page column 27, (2008/12/06)
Disclosed herein are substituted oxazolidinones of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and the methods of their use thereof.
The synthesis of N-aryl-5(S)-aminomethyl-2-oxazolidinone antibacterials and derivatives in one step from aryl carbamates
Perrault, William R.,Pearlman, Bruce A.,Godrej, Delara B.,Jeganathan, Azhwarsamy,Yamagata, Koji,Chen, Jiong J.,Lu, Cuong V.,Herrinton, Paul M.,Gadwood, Robert C.,Chan, Lai,Lyster, Mark A.,Maloney, Mark T.,Moeslein, Jeffery A.,Greene, Meredith L.,Barbachyn, Michael R.
, p. 533 - 546 (2013/09/05)
Since 1993, a significant process research and development effort directed towards the large-scale synthesis of oxazolidinone antibacterial agents has been ongoing in both Early Chemical Process Research and Development, and Chemical Process Research and Development at Pharmacia. This work has led to the successful development of the current commercial process to produce Zyvox (linezolid), recently approved by the FDA as an antibacterial. While this synthesis is appropriate for the preparation of linezolid in particular, a more convergent and versatile synthesis was developed for the rapid preparation of numerous other oxazolidinone analogues. Toward this end, economical methods for the large-scale preparation of N-[(2S)-2-(acetyloxy)-3-chloropropyl]acetamide 3 and tert-butyl [(2S)-3-chloro-2-hydroxypropyl]carbamate 27 from commercially available (S)-epichlorohydrin via the common intermediate (2S)-1-amino-3-chloro-2-propanol hydrochloride 2a were developed. Also, general methods for coupling these reagents with N-aryl carbamates to give N-aryl-5(S)-aminomethyl-2-oxazolidinone derivatives in one step were developed. These reagents and procedures have proven widely applicable in the preparation of a diverse array of oxazolidinone analogues such as 23 and 28 in both process and medicinal chemistry research.
Process to prepare oxazolidinones
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, (2008/06/13)
The present invention relates to a one-step process to prepare pharmacologically active 2-oxo-5-oxazolidinylmethylacetamides.
