145213-48-5

Basic information

• Product Name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
• Synonyms: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;1-(2-(Hydroxymethyl)oxathiolan-5-yl)-5-fluorocytosine;2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, rel-;2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, cis-;2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, cis-(+-)-;2',3',5-Ftc;3'-Thia-2'.3'-dideoxy-5-fluorocytidine;5-Fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
• CAS NO: 145213-48-5
• Molecular Formula: C8H10FN3O3S
• Molecular Weight: 0
• Mol File: 145213-48-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one(145213-48-5)
• EPA Substance Registry System: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one(145213-48-5)

Safety Data

• Hazardous Substances Data: 145213-48-5(Hazardous Substances Data)

Upstream product

• 144371-00-6 Emtricitrabine 
• 143446-69-9 cis-{5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl}methyl butanoate 
• 144371-00-6 (+/-)-cis-2',3'-dideoxy-5-fluoro-3'-thiacytidine 
• 149819-36-3 (+)-(2S,5R)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine 
• 144371-00-6 trans-2-hydroxymethyl-5-(5'-fluorocytosin-1'-yl)-1,3-oxathiolane 
• 149819-37-4 (-)-(2S,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine 
• 145986-20-5 (+)-(2R,5R)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 1321928-76-0 4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt 
• 1321928-75-9 5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester 

Downstream Products

• 137530-41-7 racivir 
• 144371-00-6 (+)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane 
• 144371-00-6 (-)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane 
• 144371-00-6 (-)-(2S,5S)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 144371-00-6 (+)-(2R,5R)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 1365246-91-8 C₅₈H₇₂F₂N₆O₁₂S 
• 1365246-86-1 (-)-N₄-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine 
• 1365246-85-0 (-)-5'-O-(t-butyldimethylsilyl)-N₄-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine 
• 1365246-84-9 4-amino-1-((2R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one 

Relevant articles and documents

Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation

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)

Preparation method for emtricitabine isomer

The invention discloses a preparation method for an embritabine isomer. The preparation method comprises the following steps: with Solketal as a starting material, allowing the Solketal to undergo a six-step reaction of esterification, hydrolysis, oxidation, condensation cyclization, acetylation and glycosylation condensation so as to synthesize four mixture intermediates of emtricitabine; and splitting the four isomer intermediates into a cis-isomer mixture and a trans-isomer mixture through a chiral reagent. According to the invention, by adoption of a simple starting material, a mixture forsplitting key intermediates of four optical isomers of the emtricitabine is synthesized through the six-step reaction, and chiral acid is utilized to split the four isomers into a mixture of cis andtrans isomers, so the preparation method provided by the invention has the advantages of simple and convenient operation, high yield and high isomer chiral purity.

Asymmetric preparation method for Emtricitabine

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.

Preparation method of emtricitabine (by machine translation)

The synthesis cost of the emtricitabine is greatly reduced, the synthetic process is simple, 5 - the (S)- (+) - synthesis conditions are mild, the chiral substrate is easily removed in the synthesis process, 2,5 - the generated triwaste pollutants are few, and the entreabine is suitable for large-scale production of entreabine 5 . (by machine translation)

Asymmetric synthesis method of emtricitabine

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.

A Suitqable to preparation method

The invention discloses a Suitqable to preparation method. Refined pure 5 S - (5 '- fluorocytosine yl - 1') - 1, 3 - oxathiolane - 2 - ethoxy carbonyl - (1 'R, 2'S, 3' R) - menthyl ester; in the weak base and the solvent removed under the condition of chiral L - menthol get products Suitqable to. The invention required the starting raw material is cheap, mild reaction conditions, the atom utilization rate is high, the operation technique is simple, the reagents used in the environmental protection, the resulting high purity, reach the medical standard, is suitable for the industrial production of kindness or gemcitabine.

Emtricitabine synthesis method

The invention provides an emtricitabine synthesis method, which comprises: carrying out condensation on cheap and easily available dihaloacetic acid as a raw material and L-menthol, hydrolyzing to obtain menthyl glyoxylate hydrate, condensing with 2,5-dihydroxy-1,4-dithiane, carrying out halogenation, coupling with silylated 5-flucytosine, reducing, carrying out salt forming with salicylic acid toobtain emtricitabine salicylate, and finally re-crystallizing to obtain optically pure emtricitabine. According to the present invention, the whole synthesis process has characteristics of inexpensive and easily available raw materials, simple synthesis process and mild synthesis conditions, such that the synthesis cost of emtricitabine is substantially reduced; various raw materials have characteristics of good reaction selectivity and high utilization rate, such that the yield of the obtained emtricitabine is high; and the chiral substrate is easily removed during the synthesis, and the generated three-waste pollutants are less, such that the method is suitable for industrial large-scale production of emtricitabine.

Benzoic acid Suitqable to salt, its preparation method and uses the benzoic acid Suitqable to salt preparation Suitqable to method

The invention discloses emtricitabine benzoate, a preparation method thereof, and a method of preparing emtricitabine from emtricitabine benzoate, and belongs to the biochemistry field. Emtricitabine benzoate is a novel compound, has not been reported before, and is not recorded in any product catalogue. The emtricitabine benzoate is prepared by combining benzoic acid and emtricitabine in a water phase or an organic phase. When benzoic acid and emtricitabine are combined in a water phase or an organic phase, emtricitabine benzoate can be easily separated from the reaction system. By adding organic base or inorganic base into the water phase/organic phase reaction system, emtricitabine benzoate can be decomposed to obtain emtricitabine. By preparing emtricitabine from emtricitabine benzoate, after the reactions, emtricitabine can be easily separated from the reaction system, the purity of the obtained emtricitabine is more than 99%, and the yield is usually more than 80%.

Preparation method for emtricitabine hydrohalide

The invention discloses a preparation method for emtricitabine hydrohalide. The preparation method for the emtricitabine hydrohalide provided by the invention comprises the following steps: subjecting crude emtricitabine and hydrogen halide to a salt-forming reaction in an alcohol solvent so as to obtain emtricitabine hydrohalide, wherein the HPLC purity of the crude emtricitabine is larger than 85%; the hydrogen halide is selected from the group consisting of hydrogen chloride, hydrogen bromide or hydrogen iodide; and X is selected from the group consisting of chlorine, bromine or iodine. The preparation method provided by the invention has the advantages of simple operation, simple and convenient postprocessing and high yield; and the prepared emtricitabine product has high purity, can reach standards of raw medicines, has an HPLC purity larger than 99.60% and a largest single impurity less than 0.10%, is low in production cost, and is applicable to industrial production.

PROCESS FOR PRODUCING LAMIVUDINE AND EMTRICITABINE

This invention provides for flow and batch synthesis processes for the production of Lamivudine and Emtricitabine, including flow and batch synthesis processes wherein at least of the synthesis steps are conducted in a solvent free environment.