851443-04-4

Basic information

• Product Name: Rosuvastatin ethyl ester
• Synonyms: ROSUVASTATIN ETHYL ESTER;7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-(N-methyl-N-methylsulfonyl-amino)-pyrimidin-5-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester;Rosuvastatin Acid Ethyl Ester;(3R,5S,E)-Ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido) pyrimidin-5-yl)-3;Rosuvastatine;(3R,5S,E)-Ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl);7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-(methyl-methylsulfonyl-amino)-pyrimidin-5-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester;Rosuvastatin Impurity 5
• CAS NO: 851443-04-4
• Molecular Formula: C₂₄H₃₂FN₃O₆S
• Molecular Weight: 509.59
• Product Categories: Rosuvastatin Calcium and its intermediates
• Mol File: 851443-04-4.mol

Chemical Properties

• Boiling Point: 699.1 °C at 760 mmHg
• Flash Point: 376.6 °C
• Appearance: /
• Density: 1.294 g/cm³
• Vapor Pressure: 1.62E-20mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.39±0.20(Predicted)
• CAS DataBase Reference: Rosuvastatin ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Rosuvastatin ethyl ester(851443-04-4)
• EPA Substance Registry System: Rosuvastatin ethyl ester(851443-04-4)

Safety Data

• Hazardous Substances Data: 851443-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Rosuvastatin ethyl ester is used as a key intermediate in the synthesis of rosuvastatin for the purpose of managing LDL cholesterol levels. This cholesterol-lowering medication is essential in the treatment and prevention of cardiovascular diseases by reducing the risk of heart attacks and strokes associated with high cholesterol levels.

InChI:InChI=1/C24H32FN3O6S/c1-6-34-21(31)14-19(30)13-18(29)11-12-20-22(15(2)3)26-24(28(4)35(5,32)33)27-23(20)16-7-9-17(25)10-8-16/h7-12,15,18-19,29-30H,6,13-14H2,1-5H3/b12-11+/t18-,19-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 503610-43-3 Rosuvastatin lactone 
• 901765-36-4 (S,E)-ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate 
• 13257-83-5 ethyl 3-trimethylsiloxy-2-butenoate 
• 141-97-9 ethyl acetoacetate 
• 890028-66-7 (E)-N-[4-(4-fluorophenyl)-6-isopropyl-5-(3-oxoprop-1-en-1-yl)pyrimidin-2-yl]-N-methyl methanesulfoneamide 
• 89186-81-2 1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene 

Downstream Products

• 1344117-94-7 (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-hydroxy-6-heptenoic acid n-propylamine salt 
• 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 
• 1332364-08-5 (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxy-N,N-dimethylhept-6-enamide 
• 287714-41-4 rosuvastatin 

Relevant articles and documents

Efficient and highly stereoselective assembly of rosuvastatin

We report an asymmetric synthesis of rosuvastatin starting from an α,β-unsaturated aldehyde precursor containing the rosuvastatin heterocyclic core at its terminus. The α,β-unsaturated carbonyl starting material was used in a highly stereoselective Ti-catalyzed aldol condensation followed by a syn-selective Narasaka–Prasad borane-ketone reduction and hydrolysis step to provide rosuvastatin calcium. This approach provides concise access to stereochemically pure rosuvastatin from simple and readily available starting materials in 3 steps. The overall three-step process provides rosuvastatin calcium in 80% yield, >99:1 syn/anti ratio, and >99% ee.

Method for synthesizing rosuvastatin ester by using continuous flow tubular reactor

The invention relates to a method for synthesizing rosuvastatin ester by using a continuous flow tubular reactor, which comprises the following steps of (1) mixing a compound 1 with a solvent to obtain a material A, (2) preparing a 0.01-0.05 mol/L sulfuric acid solution to obtain a material B, (3) respectively pumping the material A and the material B into a first tubular reactor for a chemical reaction, wherein the reaction temperature is 35-45 DEG C, and the reaction time is 40-80 s, and after the reaction is finished, adjusting the pH value of the obtained reaction solution to 6.5-7.5, and carrying out liquid separation, vacuum concentration, recrystallization, centrifugation and drying to obtain the target product.The specific synthetic route is as follows. By adopting the method disclosed by the invention, the time required by the whole reaction process is extremely short, the reaction condition is mild, and the situation that by-products are generated due to overlong reaction time or overhigh reaction temperature can be effectively avoided, so that the yield of the target product is high and reaches 97% or above, and the purity of the target product is high and reaches 99% or above.

Statins intermediate and its derivatives

The invention discloses a preparation method for a tatin intermediate and derivatives thereof. The compound adopts a structure shown in a formula I (refer to the specification); the preparation method is that a compound shown in a formula II (refer to the specification) and a nucleophile reagent are subjected to the ring-opening reaction, wherein R is a C1-10 alkoxy group. The preparation method has the advantages that the mild conditions are realized, the reaction operation is simple, the reaction time is short, the product transformation ratio is high and the method is suitable for large-scale production.

PROCESS FOR THE MANUFACTURE OF ROSUVASTATIN CALCIUM USING CRYSTALLINE ROSUVASTATIN ETHYL ESTER

The present invention relates to an improved process to prepare Rosuvastatin calcium of Formula (I), with good quality. Further, the present invention also relates to a crystalline polymorphic form of Rosuvastatin ethyl ester.

PROCESS FOR THE MANUFACTURE OF ROSUVASTATIN CALCIUM USING CRYSTALLINE ROSUVASTATIN ETHYL ESTER

The present invention relates to an improved process to prepare Rosuvastatin calcium of Formula (I), with good quality. Further, the present invention also relates to a crystalline polymorphic form of Rosuvastatin ethyl ester.

Highly stereoselective hydrogenations-as key-steps in the total synthesis of statins

Statins are inhibitors of 3-hydroxy-3-methyl-glutaryl coenzyme A reductase (HMG-CoA reductase) and became the standard of care for treatment of hypercholesterolemia because of their efficacy, safety, and long-term benefits. They are administered as diaste

PROCESS FOR THE MANUFACTURE OF ROSUVASTATIN CALCIUM WITH HIGH PURITY

The present invention relates to an improved process to prepare Rosuvastatin calcium of Formula (I), with good quality, which comprises a) reducing Rosuvastatin keto ester of Formula (III) with a hydride ion source and dialkylalkoxyborane at law temperatu

AN IMPROVED PROCESS FOR PREPARATION OF ROSUVASTATIN CALCIUM

The present invention relates to an improved process for preparing (E)-7-[4-(4-fluorophenyl)- 6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6- enoic acid calcium of Formula (I).

PROCESS FOR THE PREPARATION OF ROSUVASTATIN

A process for the manufacture of a compound of formula (V), useful for making rosuvastatin, by a stereoselective aldol reaction is described.

Synthetic Method and Intermediates of Rosuvastatin Calcium and Preparation Methods of Intermediates

The present invention publicly discloses a synthetic method and intermediates of rosuvastatin calcium and synthetic methods of the intermediates. The synthetic method uses 4-4′-fluorophenyl-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyridine-5-formalde