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New preparation method of atorvastatin calcium 1H-pyrrole derivatives

A technology of pyrrole and compound, which is applied in the field of chemical pharmaceuticals and can solve problems such as high prices

Active Publication Date: 2010-07-07
ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Expensive chiral C-5 or C-7 compounds are constraints main reason for production

Method used

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  • New preparation method of atorvastatin calcium 1H-pyrrole derivatives
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  • New preparation method of atorvastatin calcium 1H-pyrrole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Add compound 1221.0g (2.0mol), NaCN 113.5g (2.2mol), 550ml DMF, 75ml CH 3 OH, the temperature was raised to 60°C to react, the massive solid in the system gradually disappeared and a white powdery solid was formed. After reacting for 8h, it was filtered and the solid was treated with NaClO solution. The mother liquor is concentrated by distillation under reduced pressure (distillation temperature does not exceed 100°C), and the solvent in the system is evaporated to dryness as much as possible. The evaporated solvent can be recycled and used mechanically. Add 40ml of concentrated HCl to adjust the pH of the system to 1-2, and then add 200-250ml acetone, stirred, filtered, the solid was treated with NaClO solution, and the mother liquor was collected and concentrated. Distilled under reduced pressure and collected (T=130°C) fractions to obtain a yellow oily liquid. Yield: 55%

Embodiment 2

[0052] Add compound 1221.0g (2.0mol), NaCN 113.5g (2.2mol), 500ml acetonitrile, 70ml CH 3 OH, the temperature was raised to 60°C to react, the massive solid in the system gradually disappeared and a white powdery solid was formed. After reacting for 10 h, it was filtered and the solid was treated with NaClO solution. The mother liquor is concentrated by distillation under reduced pressure (distillation temperature does not exceed 100°C), and the solvent in the system is evaporated to dryness as much as possible. The evaporated solvent can be recycled and used mechanically. Add 40ml of concentrated HCl to adjust the pH of the system to 1-2, and then add 200-250ml acetone, stirred, filtered, the solid was treated with NaClO solution, and the mother liquor was collected and concentrated. Distilled under reduced pressure and collected (T=130°C) fractions to obtain a yellow oily liquid. Yield: 45%.

Embodiment 3

[0054] Compound 1221.0g (2.0mol), KCN143g (2.2mol), 600ml DMF were added to a 1L three-neck flask, and the temperature was raised to 60°C for reaction. The massive solid in the system gradually disappeared and a white powdery solid was formed. After reacting for 10 h, it was filtered and the solid was treated with NaClO solution. The mother liquor was concentrated by distillation under reduced pressure (distillation temperature did not exceed 100°C), and the solvent in the system was evaporated to dryness as much as possible. The evaporated solvent can be recycled and used mechanically. Carefully add 40ml of concentrated HCl to adjust the pH of the system to 1-2, and then add 200 - 250ml of acetone, stirred, filtered, the solid was carefully treated with NaClO solution, the mother liquor was collected and concentrated. Distilled under reduced pressure and collected (T=130°C) fractions to obtain a yellow oily liquid. Yield: 50%.

[0055] Step B

[0056]

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Abstract

The invention relates to a synthetic route and a method for preparing (R)-5-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylamino formyl-1H-pyrrole-1-ethyl)-3-hydroxyvalerate. The (R)-5-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylamino formyl-1H-pyrrole-1-ethyl)-3-hydroxyvalerate is obtained through seven steps by using (R)-2,3-dihydroxy-chloropropane as raw material. The method provided bythe invention has low cost, simple operation, and is suitable for industrialization.

Description

technical field [0001] The present invention relates to a method for preparing (R)-5-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-1H-pyrrol-1-yl) The invention discloses a synthetic route and a preparation method of 3-hydroxyvalerate, which belong to the field of chemical pharmacy. Background technique [0002] Compound (R)-5-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-1H-pyrrol-1-yl)-3-hydroxypentyl Ester is a synthetic blood lipid-lowering drug atorvastatin calcium, trade name key intermediates. The chemical name of atorvastatin calcium is [R-(R * , R * )]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-isopropyl-3-phenyl-4-formic acid phenylamide-1H-pyrrole-1-heptanoic acid calcium salt (2 : 1) trihydrate, the compound can act as a 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) inhibitor, so it can be used as a hypolipidemic and / or hypocholesterolemic drug. [0003] Patent US 4681893 discloses the preparation method of trans-6-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34
Inventor 王立新甘立新陈一徐小英王文田芳贺光云
Owner ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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