764659-79-2

Basic information

• Product Name: 5-Fluoro ent-LaMivudine Acid D-Menthol Ester
• Synonyms: 5-Fluoro ent-LaMivudine Acid D-Menthol Ester;(2S,5R)-(1S,2R,5S)-2-Isopropyl-5-Methylcyclohexyl 5-(4-aMino-5-fluoro-2-oxopyriMidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate;(5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate;Emtricitabine Impurity V;(5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1
• CAS NO: 764659-79-2
• Molecular Formula: C18H26FN3O4S
• Molecular Weight: 399.4801432
• Product Categories: Carbohydrates & Derivatives;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Carbohydrates & Derivatives, Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 764659-79-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 508.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.40±0.10(Predicted)
• CAS DataBase Reference: 5-Fluoro ent-LaMivudine Acid D-Menthol Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro ent-LaMivudine Acid D-Menthol Ester(764659-79-2)
• EPA Substance Registry System: 5-Fluoro ent-LaMivudine Acid D-Menthol Ester(764659-79-2)

Safety Data

• Hazardous Substances Data: 764659-79-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the synthesis of ent-Emtricitabine (E525005).

Upstream product

• 111878-21-8 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine 
• 147027-09-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 1309459-32-2 5-hydroxy-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methylcyclohexyl ester 
• 26315-61-7 L-menthyl glyoxylate 
• 21758-30-5 (1R,2S,5R)-(-)-menthyl dichloroacetate 
• 2216-51-5 (-)-menthol 
• 2022-85-7 Flucytosine 
• 200396-19-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate 
• 111969-64-3 L-menthyl glyoxylate monohydrate 
• 1321928-66-8 5-(pyridin-2-yloxy)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester 
• 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 
• 1144099-18-2 (1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate 
• 147126-62-3 (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester 
• 288325-76-8 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester 

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 process of emtricitabine intermediate

The invention discloses a preparation process of an emtricitabine intermediate, namely (2R,5S)-5-(5'-fluoro-cytosine-1-yl)-1,3-dioxathiolane-2-carboxylic acid-L-menthyl ester shown as a structural formula (I). The preparation process comprises the following steps: (A) taking 5-fluorocytosine shown as a structural formula 7 as a raw material, and enabling the 5-fluorocytosine to react with N,N-dimethylformamide shown as a structural formula 20 and hexamethyldisilazane shown as a structural formula 8 to prepare 2-O-trimethylsilyl-4-N-[(N',N'-dimethyl)amino]methylene-5-fluorocytosine shown as a structural formula 21; (B) condensing the compound 21 and a chlorine substitute shown as a structural formula 6 to generate (2R,5S)-5-(4'-N-((N',' dimethyl)amino)methylene-5'-fluoro-cytosine-1-yl)-1,3-dioxathiolane-2-carboxylic acid-L-menthyl ester shown as a structural formula 22; and (C) hydrolyzing the compound 22 in an acidic solution to prepare the compound I. According to the preparation process, side reaction can be reduced so that the purity of a product is improved and the consumption of raw materials is reduced. The formula (I) is as shown in the specification.

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.