Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate

Base Information

• Chemical Name: Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate
• CAS No.: 147118-39-6
• Molecular Formula: C23H28FN3O6S
• Molecular Weight: 493.556
• Mol file: 147118-39-6.mol

Synonyms:6-Heptenoicacid,7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3-hydroxy-5-oxo-,methyl ester, [R-(E)]-;(3R,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3-hydroxy-5-oxo-6-heptenoic acid methyl ester;

Chemical Property of Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate

Chemical Property:

• Vapor Pressure: 1.15E-20mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 701.68 °C at 760 mmHg
• PKA: 12.87±0.20(Predicted)
• Flash Point: 378.163 °C
• PSA: 135.14000
• Density: 1.311 g/cm³
• LogP: 3.77910
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

5-OxorosuvastatinMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-Oxorosuvastatin methyl ester is an intermediate in the synthesis of Rosuvasatatin (calcium salt: R700500), a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor that decreases high-sensitivity C-reactive protein (hsCRP) and cholesterol concentrations in the blood.

Technology Process of Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate

There total 23 articles about Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)-pyrimidin-5-yl)-(3R)-3-tert-butyldimethylsiloxy-5-oxo-(E)-6-heptenoic acid methyl ester (147118-38-5) → methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate (147118-39-6)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 0 - 20 ℃; for 1.5h;

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl-methyl-amino)pyrimidin-5-yl]-5-oxo-hept-6-enoic acid methyl ester → methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate (147118-39-6)

Guidance literature:

With methanesulfonic acid; In water; acetonitrile; at 20 - 30 ℃; for 15h;

Reference yield:

methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate (147118-35-2) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate (147118-39-6)

Guidance literature:

methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate; N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide; In acetonitrile; for 20h; Reflux;

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 3h; Cooling with ice;

With sodium hydrogencarbonate; In dichloromethane; water; acetonitrile;

upstream raw materials:

7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)-pyrimidin-5-yl)-(3R)-3-tert-butyldimethylsiloxy-5-oxo-(E)-6-heptenoic acid methyl ester

4-fluorobenzaldehyde

(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester

ethyl 4-methyl-3-oxo-pentanoate

Downstream raw materials:

rosuvastatin 1-naphthalen-1-yl-ethylamine salt

rosuvastatin (R)-1-(1-naphthyl)ethylamine

7-[4-(4-fluorophenyl)-6-isopropyl-2(N-methyl-N-methanesulfonamido)pyrimidin-5-yl]-(3R)-3-hydroxy-5-carbonyl-6-(E)-heptenoic acid

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine

Refernces

• 1、 -. "Preparing rosuvastatin calcium intermediates". Paragraph 0012; 0034; 0038-0040; 0046; 0052; 0058; 0064. . Retrieved 2017/08/25.
• 2、 -. "PROCESS FOR THE PREPARATION OF ROSUVASTATIN CALCIUM VIA NOVEL AMINE INTERMEDIATE". Page/Page column 17. . Retrieved 2012/05/31.