ChemicalBook CAS DataBase List Rosuvatatin Impurity 24

Rosuvatatin Impurity 24 synthesis

6synthesis methods

Product Name:Rosuvatatin Impurity 24
CAS Number:894787-93-0
Molecular formula:C25H32FN3O6S
Molecular Weight:521.6

1,3-Dioxane-4-acetic acid, 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-, ethyl ester, (4R,6S)-

851440-18-1
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894787-93-0
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Yield:894787-93-0 95%

Reaction Conditions:

Stage #1: 6-((1E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(methylsulfonyl)amino)pyrimidin-5-yl)ethenyl)-2,2-dimethyl-1,3-dioxan-4yl acetic acid ethyl esterwith sodium hydroxide in tetrahydrofuran;water at 90 - 100;
Stage #2: with hydrogenchloride in water;Cooling with ice;

Steps:

2

Example 2; (6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl-methyl-amino)-pyrimidin-5-yl]-vinyl}-(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid; (6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl-methyl-amino)-pyrimidin-5-yl]-vinyl}-(4R,6S)-2,2-dimethyl-[1,3]dioxane-4-yl)-acetic acid ethylester (5.52g, 10 mmol) was dissolved in tetrahydrofuran (10 ml) and 1M sodium hydroxide 30 ml, 30 mmol) was added to the solution by stirring and it was heated to 90-100 °C. The reaction mixture was kept at this temperature until the parent material is transformed (ca. 4-6 hours). (It was analyzed by thin layer chromatography on silica gel in toluol-ethyl acetate (6:1)). The reaction mixture was diluted with ethyl-acetate (50 ml), the aqueous phase was separated and the organic phase was extracted with water (20 ml) then the organic phase was concentrated in vacuum. Water (100 ml) was added to the residue and the solution was treated with 1 M hydrogen chloride solution by cooling with ice-cold water. The precipitated product was filtered off, washed with cold water (2x 50 ml) and dried at 50 °C. Yield: 4.9 g (95%) Melting point: 172-174 °C

References:

EP1902036,2010,B1 Location in patent:Page/Page column 8