145213-48-5Relevant articles and documents
Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation
Mear, Sarah Jane,Nguyen, Long V.,Rochford, Ashley J.,Jamison, Timothy F.
, p. 2887 - 2897 (2022/02/07)
By simple combination of water and sodium iodide (NaI) with chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water)
Asymmetric preparation method for Emtricitabine
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Paragraph 0028; 0036; 0038, (2019/11/21)
The invention provides an asymmetric preparation method for Emtricitabine. The preparation method comprises the steps of subjecting L-menthyl chloroformate, which serves as a raw material, to condensation with 2-halo ethanol, carrying out oxidation so as to obtain a stable intermediate, i.e., an aldehyde alcohol menthyl ester, subjecting the intermediate to condensation with 2,5-dihydroxyl-1,4-dithiane, carrying out halogenation, then, carrying out coupling with silanized 5-flucytosine, then, carrying out hydrolyzing, then, carrying out salt forming with salicylic acid, and finally, carrying out recrystallization, thereby obtaining purified Emtricitabine. According to the method, raw materials employed in a whole synthesis process are cheap and readily available, thus, the synthesis cost of the Emtricitabine disclosed by the invention is reduced greatly, the synthesis process is simple, the synthesis conditions are moderate, and the obtained Emtricitabine is relatively high in yield; and meanwhile, a chiral substrate is easy to remove during synthesis, produced pollutants, i.e., waste gases, waste water and waste residues are few, and thus, the method is applicable to industrial large-scale production of the Emtricitabine.
Asymmetric synthesis method of emtricitabine
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Paragraph 0027; 0028; 0034-0036, (2019/10/29)
The present invention provides an asymmetric synthesis method of emtricitabine. L-menthyl chloroformate is used as raw material to condense with 2-chloro-1-ethanol, then hydrolyze under the conditionof catalyst to obtain acetaldehyde alcohol optically active ester which is then induced by chiral promoter to condense with 2, 5-dihydroxyl-1,4-dithiane to give trans 5-hydroxyl-1,3-oxythiacyclopentane-2-methyl-L-menthol carbonate, the trans 5-hydroxyl-1,3-oxythiacyclopentane-2-methyl-L-menthol carbonate is halogenated and coupled with silanized 5-fluorocytosine, emtricitabine is obtained by removing the chiral auxiliary agent under the condition of weak alkalinity. As that raw materials used in the whole synthesis process are cheap and easy to obtain, the raw material utilization ratio is high, so that the synthesis cost of the emtricitabine is greatly reduced, and the synthesis process is simple, the synthesis condition is mild, the yield of the obtained emtricitabine is high, meanwhile,the chiral assistant is easy to remove in the synthesis process, the three waste pollutants generated are less, and the preparation method is suitable for the large-scale industrial production of theemtricitabine.