(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Product Name: (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
CAS No.: 764659-72-5
Chemical Name: (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
Synonyms: Emtricitabine Menthyl Ester Impurity;(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxa...;(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid;(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S;(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-;Emtricitabine L-Menthyl Ester ((2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-;[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolane-2-carboxylate;(2R,5S)-(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl 5-(4-aMino-5-fluoro-2-oxopyriMidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate;(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylate;(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
CBNumber: CB42502643
Molecular Formula: C18H26FN3O4S
Formula Weight: 399.48
MOL File: 764659-72-5.mol

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(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester Property

Melting point:: 190 - 192°C
Boiling point:: 508.5±60.0 °C(Predicted)
Density: 1.47
storage temp.: Refrigerator
solubility: Chloroform (Slightly), DMSO (Sparingly, Heated), Methanol (Slightly, Sonicated)
pka: 2.40±0.10(Predicted)
form: Solid
color: Off-White to Pale Brown
optical activity: -138.5°(C=0.01g/mI, CHCL3 , 20°C, 589nm)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: A609705
Product name: (2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylicAcid(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexylEster
Packaging: 1g
Price: $945
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 53778
Product name: (2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylicAcid(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexylEster
Packaging: 1g
Price: $1275
Updated: 2021/12/16

Chemenu

Product number: CM166684
Product name: (2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylicacid(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexylester
Purity: 95%
Packaging: 25g
Price: $102
Updated: 2021/12/16

Chemenu

Product number: CM166684
Product name: (2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylicacid(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexylester
Purity: 95%
Packaging: 100g
Price: $262
Updated: 2021/12/16

Crysdot

Product number: CD11060596
Product name: (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
Purity: 95+%
Packaging: 100g
Price: $277
Updated: 2021/12/16

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(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester Chemical Properties,Usage,Production

Chemical Properties

(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester is Off-White Solid

Uses

(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester is an intermediate in the synthesis of Emtricitabine (E525000). A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).

Synthesis

2022-85-7

147027-09-6

764659-72-5

3-thiane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester in the following general steps: 1. 6-Amino-5-fluoropyrimidin-2(1H)-one (22.4 g, 0.173 mol, 1.1 mole equivalents), hexamethyldisilazane (HMDS) (100 ml, 0.477 mol, 3.1 mole equivalents), and trimethylmethylsilanedichloro (TMSCL) (11.2 ml) were mixed at 25-30 °C, protected by nitrogen. 2. The reaction mixture was heated to 120-130 °C until a clarified solution was formed, followed by removal of excess solvent by vacuum distillation at 90-100 °C to afford a methylsilylated 6-amino-5-fluoropyrimidin-2(1H)-one residue. 3. The above residue was cooled to room temperature and dissolved by addition of fresh dichloromethane (100 ml) to give Solution A. 4. In another flask, (2R,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate (50 g, 0.151 mol, 1.0 mole equivalent), dichloromethane (250 ml) and zirconium tetrachloride (ZrCl4) (17.6 g, 0.075 mol, 0.5 molar equivalents) were mixed under nitrogen protection to obtain solution B. 5. Solution A was slowly added to solution B at 25-30 °C and the reaction mixture was stirred at the same temperature for 6 h. The reaction process was monitored by HPLC or thin layer chromatography. 6. After completion of the reaction, the reaction mixture was cooled to 10-20 °C and pre-cooled (10-20 °C) water (250 ml) was added under stirring. 7. The pH was adjusted to 8-8.5 using triethylamine and the organic and aqueous layers were separated and the organic layer was washed with 250 ml of water. 8. The organic layer was concentrated under vacuum to obtain a residue, which was dissolved in methanol (200 ml) and n-heptane (100 ml) with stirring. 9. The solution was added to water (200 ml) and the separated solid was filtered and washed sequentially with water and n-heptane. 10. The solid was dried under vacuum at 40-45 °C to give 48.5 g of the target product in 80% yield and 99.94% chiral purity.

References

[1] Organic Letters, 2015, vol. 17, # 11, p. 2626 - 2629
[2] Patent: WO2013/21290, 2013, A1. Location in patent: Page/Page column 24; 25

(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester Suppliers

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View Lastest Price from (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester manufacturers

Career Henan Chemical Co

Product: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolane-2-carboxylate 764659-72-5
Price: US $3.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100kg
Release date: 2019-08-07

Shanghai Yingrui Biopharma Co., Ltd.

Product: (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester 764659-72-5
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100t
Release date: 2018-03-06

764659-72-5, (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl esterRelated Search:

Emtricitabine Impurity 25 3alpha-Hydroxy-7-oxo-5beta-cholanic Acid LITHOCHOLIC ACID (+)-ISOMENTHOL (2R,5S)-5-(5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester (2S)-2-[[[(1,1-Dimethylethyl)diphenylsilyl]oxy]methyl]-1,3-oxathiolan-5-ol 5-Acetate Emtricitabine Impurity 18 Emtricitabine Impurity 5-fluoro-1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)cytosine 5-epi EMtricitabine Ursodeoxycholic acid 2,4(1H,3H)-Pyrimidinedione,5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2S-cis)- (9CI) Emtricitabine Emtricitabine Impurity 8 ISOPULEGOL, TECH. 156198-94-6 EMTRICITABINE-13C,15N2 (-)-EMtricitabine S-Oxide (Mixture of DiastereoMers)

(2R,5S)-(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl 5-(4-aMino-5-fluoro-2-oxopyriMidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate

(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Emtricitabine impurity 9/Emtricitabine Menthyl Ester/(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester

[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolane-2-carboxylate

(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-

Emtricitabine Menthyl Ester Impurity

(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid

(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S

1,3-Oxathiolane-2-carboxylic acid, 5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2R,5S)-

(2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxa...

TIANFU-CHEM (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

Emtricitabine L-Menthyl Ester ((2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester)

(2R,5S)-5- (4-Amino-5-fuoro-2-oxo-1(2H)-pyrimidinyl-1 / yl)-[1.3] oxathiolanc-2-carboxylic acid(IR,2S,5R)-5 methyl-2- (1-methylethyl) cyelohexyl ester (FCME)

(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

Emtricitabine L-Menthyl Ester ((2R,5S)-5-(4-Amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-

764659-72-5

C18H26N3O4FS