147118-40-9

Basic information

• Product Name: Rosuvastatin methyl ester
• Synonyms: 7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-(N-methyl-N-methylsulfonyl-amino)-pyrimidin-5-yl]-3,5-dihydroxy-hept-6-enoic acid methyl ester;(3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-Methylethyl)-2-[Methyl(Methylsulfonyl)aMino]-5-pyriMidinyl]-3,5-dihydroxy-6-heptenoic Acid Methyl Ester;N-Methyl acetaMidc 7-[4-(4-flucrophenyl)-6-iso-propyl-2-(N-Methyl-N-Methyl sulfonyleMino) pyriMidin-5-yl[ -(3R,5S)-dihydroxy-(e)- 6-hepteeoate;Rosuvastatin Acid Methyl Ester;(3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)-amino]-5-pyrimidinyl;6-Heptenoic acid,7-[4-(4-fluorophenyl)-6-(1-Methylethyl)-2-[Methyl(Methylsulfonyl)aMino]-5-pyriMidinyl]-3,5-dihydroxy-,Methyl ester, (3R,5S,6E)-;(3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)-amino]-5-pyrimidi;(3R,5S,E)-methyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate
• CAS NO: 147118-40-9
• Molecular Formula: C₂₃H₃₀FN₃O₆S
• Molecular Weight: 495.57
• EINECS: 1312995-182-4
• Product Categories: Rosuvastatin Calcium and its intermediates;Rosuvastatin intermediates;Aromatics;Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 147118-40-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 692.3 °C at 760 mmHg
• Flash Point: 372.5 °C
• Appearance: /
• Density: 1.313 g/cm³
• Vapor Pressure: 4E-20mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.33±0.20(Predicted)
• CAS DataBase Reference: Rosuvastatin methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Rosuvastatin methyl ester(147118-40-9)
• EPA Substance Registry System: Rosuvastatin methyl ester(147118-40-9)

Safety Data

• Hazardous Substances Data: 147118-40-9(Hazardous Substances Data)

Usage

Description

Rosuvastatin methyl ester is a white solid that is identified as an impurity of Rosuvastatin (R700500) in pharmaceutical dosage forms under forced degradation conditions. It is a derivative of the widely used cholesterol-lowering drug, Rosuvastatin, and is formed as a result of chemical modifications in the manufacturing process or during the degradation of the parent compound.

Uses

Used in Pharmaceutical Industry:
Rosuvastatin methyl ester is used as an impurity in the pharmaceutical industry for Rosuvastatin dosage forms. The presence of this impurity is significant as it can impact the efficacy, safety, and quality of the final drug product. It is essential to monitor and control the levels of Rosuvastatin methyl ester during the manufacturing process to ensure the therapeutic benefits of Rosuvastatin are not compromised.
Additionally, understanding the properties and behavior of Rosuvastatin methyl ester can aid in the development of improved drug delivery systems and formulations, potentially enhancing the bioavailability and effectiveness of Rosuvastatin in treating hypercholesterolemia and related cardiovascular conditions.
Used in Research and Development:
Rosuvastatin methyl ester serves as a valuable compound for research and development purposes in the pharmaceutical sector. It can be used to study the degradation pathways of Rosuvastatin, understand the factors that contribute to its formation, and develop strategies to minimize its presence in the final drug product. This knowledge can contribute to the improvement of manufacturing processes, quality control measures, and the overall safety and efficacy of Rosuvastatin-based treatments.

InChI:InChI=1/C23H30FN3O6S/c1-14(2)21-19(11-10-17(28)12-18(29)13-20(30)33-4)22(15-6-8-16(24)9-7-15)26-23(25-21)27(3)34(5,31)32/h6-11,14,17-18,28-29H,12-13H2,1-5H3/b11-10+/t17-,18-/m1/s1

Upstream product

• 67-56-1 methanol 
• 147118-27-2 ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate 
• 147118-32-9 5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 122930-45-4 (E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester 
• 459-57-4 4-fluorobenzaldehyde 
• 147118-39-6 methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate 
• 503610-43-3 Rosuvastatin lactone 
• 124752-23-4 tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 289042-12-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester 
• 851440-19-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid methyl ester 
• 164576-45-8 (4R-cis)-6-formyl-2,2-dimethyl-1,3-dioxane-4-acetic acid methyl ester 
• 140164-51-8 methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate 
• 171523-71-0 (+)-(3R,5S)-Methyl 6-acetoxy-3,5-(isopropylidenedioxy)hexanoate 

Downstream Products

• 1353050-09-5 (3R,5S,E)-methyl 3,5-bis(tert-butyldimethylsilyloxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)hept-6-enoate 
• 1353050-10-8 (3R,5S,E)-3,5-bis(tert-butyldimethylsilyloxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)hept-6-enoic acid 
• 1353050-11-9 (3R,5S,E)-((R)-5,6-dinitrooxyhexyl) 3,5-bis(tert-butyldimethylsilyloxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)hept-6-enoate 
• 1353050-31-3 (3R,5S,E)-((R)-5,6-bis(nitrooxy)hexyl) 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate 
• 1416820-71-7 rosuvastatin (R)-1-(1-naphthyl)ethylamine 
• 1197348-98-3 3-methylbutyl (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate 
• 852820-97-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine 
• 1388654-77-0 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid 4-methylpentan-2-yl ester 
• 503610-43-3 Rosuvastatin lactone 
• 917805-74-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine 
• 1019876-66-4 (+)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl-methyl-amino)-pyrimidin-5-yl)-(3R,5S,6E)-dihydroxy-hept-6-enoic acid n-butylamide 
• 1374771-96-6 rosuvastatin, S-benzylisothiourea salt 
• 287714-41-4 rosuvastatin 
• 851440-19-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid methyl ester 

Relevant articles and documents

Synthetic studies on statins. Part 3: A facile synthesis of rosuvastatin calcium through catalytic enantioselective allylation strategy

A concise and stereocontrolled synthesis of rosuvastatin calcium has been accomplished, with the key steps including a Keck enantioselective allylation of chloroacetaldehyde with allyltributylstannane to install 5R-stereocenter and a VO(acac)2-catalyzed syn-diastereoselective epoxidation of (S)-1-chloropent-4-en-2-ol to set the requisite 3R-chirality.

Preparation process of rosuvastatin calcium preparation

The invention provides a preparation process of a rosuvastatin calcium preparation, and belongs to the technical field of pharmaceutical preparations. With (3R)-tert-butyldimethylsiloxy-5-oxy-6-triphenylphosphoranylidene methyl caproate and 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)pyridine-5-formaldehyde as initial raw materials, wittig reaction, deprotection reaction, chiral reduction reaction, hydrolysis reaction and purification are carried out so as to obtain a rosuvastatin calcium crude drug; then the rosuvastatin calcium crude drug is uniformly mixed with a diluent, a disintegrating agent, a stabilizing agent and a lubricant so as to obtain a mixture, and then the mixture is tabletted so as to obtain the rosuvastatin calcium preparation. The preparation process of the rosuvastatin calcium preparation disclosed by the invention has the advantages of simple operation, high yield, low cost and stable quality.

Synthetic method of rosuvastatin

The invention provides a synthetic method of rosuvastatin. The method is characterized in that butyl rosuvastatin is esterified in the presence of a neutral titanate catalyst to prepare methyl rosuvastatin. The method has the advantages of low cost and high yield, and provides a new valued approach for synthesis of the methyl rosuvastatin.