N-[4-(4-Fluorophenyl)-6-(1-methylethyl)-5-[(1E)-2-[(2S,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethenyl]-2-pyrimidinyl]-N-methylmethanesulfonamide

Base Information

• Chemical Name: N-[4-(4-Fluorophenyl)-6-(1-methylethyl)-5-[(1E)-2-[(2S,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethenyl]-2-pyrimidinyl]-N-methylmethanesulfonamide
• CAS No.: 503610-43-3
• Molecular Formula: C22H26FN3O5S
• Molecular Weight: 463.53
• Mol file: 503610-43-3.mol

Synonyms:N-[4-(4-Fluorophenyl)-6-(1-methylethyl)-5-[(1E)-2-[(2S,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethenyl]-2-pyrimidinyl]-N;N-[4-(4-fluorophenyl)-5-[(E)-2-[(2S,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]vinyl]-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide;

Chemical Property of N-[4-(4-Fluorophenyl)-6-(1-methylethyl)-5-[(1E)-2-[(2S,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethenyl]-2-pyrimidinyl]-N-methylmethanesulfonamide

Chemical Property:

• Melting Point: 131 °C
• Boiling Point: 694.955 °C at 760 mmHg
• PKA: 13.22±0.40(Predicted)
• Flash Point: 374.095 °C
• PSA: 118.07000
• Density: 1.387 g/cm³
• LogP: 3.96240
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

RosuvastatinLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An isomer of Rosuvastatin Lactone (R700500); intermediate in the production of Rosuvastatin (R700500) derivatives. Rosuvastatin Lactone (Rosuvastatin EP Impurity D) is an intermediate in the production of Rosuvastatin (R700500) derivatives.

Technology Process of N-[4-(4-Fluorophenyl)-6-(1-methylethyl)-5-[(1E)-2-[(2S,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethenyl]-2-pyrimidinyl]-N-methylmethanesulfonamide

There total 40 articles about N-[4-(4-Fluorophenyl)-6-(1-methylethyl)-5-[(1E)-2-[(2S,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethenyl]-2-pyrimidinyl]-N-methylmethanesulfonamide 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: 94.0%

N-(5-((E)-2-((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)vinyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide → Rosuvastatin lactone (503610-43-3)

Guidance literature:

With acetic acid; tetra-n-butylammoniumfluoride trihydrate; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1021/jo101050z

Reference yield: 87.0%

C50H60F2N6O12S2 → Rosuvastatin lactone (503610-43-3)

Guidance literature:

With hydrogenchloride; In water; toluene; at 20 ℃; for 8h; pH=3;

Reference yield: 82.0%

2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)- 1,3-dioxan-4-yl)acetic acid → Rosuvastatin lactone (503610-43-3)

Guidance literature:

With hydrogenchloride; phosphoric acid; In water; toluene; at 20 ℃; for 6h; pH=3;

upstream raw materials:

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

tertiary-butyl (6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]ethenyl}-(4R,6S)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

rosuvastatin methylamine salt

rosuvastatin tert-butyl ester

Downstream raw materials:

(3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxy-N-methylhept-6-enamide

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

ethyl (3R),(5S),(6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-3,5-dihydroxy-6-heptenoate

(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid methyl ester

Refernces

• 1、 -. "Synthesis method of rosuvastatin calcium". Paragraph 0056-0058. . Retrieved 2019/06/30.
• 2、 -. "NOVEL CLASS OF COMPOUNDS FOR THE TREATMENT OF CARDIOVASCULAR DISEASE". Page/Page column 41. . Retrieved 2017/09/05.