- Salts and ionic liquid of the antituberculosis drug S,S-ethambutol
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A salt screen of the antituberculosis chiral basic drug Ethambutol with protic acids resulted in the formation of several salts and an ionic liquid. The protic salt/ionic liquid product was characterized by spectroscopic (ATR-IR and ss-NMR), thermal (DSC and TGA), and X-ray diffraction. Similar to the marketed Ethambutol dihydrochloride salt of the drug, all the new salts were found to be hygroscopic. Moisture-free conditions of the desiccator and rotavapor gave nonhygroscopic materials in a few cases. X-ray crystal structures of two new salts were determined and that of the Ethambutol base and Ethambutol dihydrochloride salt were redetermined in this work.
- Cherukuvada, Suryanarayan,Nangia, Ashwini
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Read Online
- Preparation method of ethambutol
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The invention relates to a preparation method of an antituberculosis drug ethambutol. The preparation method specifically comprises the following steps: a, reacting 2-amino-1 butanol with carbonic ester to generate a compound 2, b, reacting the compound 2 with dihalogenated ethane to generate a compound 3, and c, hydrolyzing the compound 3 to generate ethambutol. According to the preparation method of the ethambutol, the adopted raw materials are low in price and easy to obtain, and the method has the advantages of short synthetic route, novel route, high yield and no dangerous process.
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Paragraph 0034-0037
(2020/11/12)
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- Preparation ethylamine butanol and ethylamine hydrochloride butanol
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The invention provides methods for preparing ethambutol and ethambutol hydrochloride. The method for preparing the ethambutol comprises the step of utilizing (S)-2-aminobutanol and 1,2-dichloroethane to perform condensation reaction to prepare the ethambutol, wherein the condensation reaction is carried out in a low-boiling organic solvent, and HCl produced in the ammonia gas neutralization reaction process is utilized. Through the utilization of the method, the ethambutol of which the yield coefficient is improved can be obtained, so that the ethambutol hydrochloride of which the yield coefficient is improved can be obtained. Besides, the methods are simple in technology, safe, stable, low in cost and super-high in practical value in the industry.
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Paragraph 0047; 0100-0101
(2017/02/28)
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- SUBSTITUTED AMINO ALCOHOLS
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Disclosed herein are substituted amino alcohol anti-mycobacterial agents and/or chelation therapy agents of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 26
(2009/04/24)
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- Enantioselective synthesis of (S,S)-ethambutol using proline-catalyzed asymmetric α-aminooxylation and α-amination
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An efficient enantioselective synthesis of (S,S)-ethambutol, a tuberculostatic antibiotic, has been achieved in 99% ee via both proline-catalyzed α-aminooxylation and α-amination of n-butyraldehyde as the key step.
- Kotkar, Shriram P.,Sudalai, Arumugam
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p. 1738 - 1742
(2007/10/03)
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- Efficient synthesis of (S,S)-ethambutol from L-methionine
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Starting from readily available amino acid L-methionine, an efficient synthesis of the tuberculostatic agent (S,S)-ethambutol has been developed. The key steps in the synthetic sequence involve: dimerization of methionine methyl ester through oxalyl diamide formation, Raney nickel desulfurization of the terminal thiomethyl groups, and a one-pot exhaustive reduction of the oxalamide and the diester functionalities to afford the desired enantiopure (S,S)-ethambutol in good overall yield.
- Stauffer, Christina S,Datta, Apurba
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p. 9765 - 9767
(2007/10/03)
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- Dynamic kinetic asymmetric transformation of diene monoepoxides: A practical asymmetric synthesis of vinylglycinol, vigabatrin, and ethambutol
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The ability to perform a dynamic kinetic asymmetric transformation (DYKAT) using the palladium-catalyzed asymmetric allylic alkylation (AAA) is explored in the context of butadiene monoepoxide. The versatility of this commercially available, but racemic, four-carbon building block becomes significantly enhanced via conversion of both enantiomers into a single enantiomeric product. The concept is explored in the context of a synthesis of vinylglycinol with phthalimide as the nitrogen source. The success of the project required a new design of the ligand for palladium wherein additional conformational restraints were introduced. Thus, the phthalimide derivative of vinylglycinol was obtained in nearly quantitative yield and had an ee of 98% which, upon crystallization, was enhanced to > 99%. This one-step synthesis of a protected form of vinylglycinol provided short practical syntheses of the title compounds. Vigabatrin requires only four steps, and ethambutol six. The intermediate to the existing synthesis of ethambutol is available in 87% yield in three steps. (R)-Serine derives from oxidative cleavage of the double bond. The reaction of phthalimide and isoprene monoepoxide demonstrates the remarkable ability of the chiral ligands to control both regioselectivity and enantioselectivity and demonstrates the effectiveness of this protocol in creating a quaternary center asymmetrically.
- Trost, Barry M.,Bunt, Richard C.,Lemoine, Remy C.,Calkins, Trevor L.
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p. 5968 - 5976
(2007/10/03)
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