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
• Article Data: 13

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

Rosuvastatin ethyl ester (CAS# 851443-04-4) is an intermediate formed during the synthetic preparation of rosuvastatin, a pharmaceutical used to manage LDL cholesterol.

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 
• 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 
• 901765-36-4 (S,E)-ethyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-hydroxy-3-oxohept-6-enoate 

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.

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.