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.
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.
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.