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Preparation method for synthesizing intermediate compound of rosuvastatin calcium

A technology for rosuvastatin calcium and intermediates, applied in the field of drug synthesis and chemical engineering, can solve the problems of high production cost, increased cost, high price, etc., and achieve the goal of avoiding the process of column chromatography separation and purification, reducing cost and simplifying steps Effect

Active Publication Date: 2009-11-25
安徽美诺华药物化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore this method needs to increase the consumption of reaction raw material, has increased the cost of production, and the anhydrous magnesium chloride used in posttreatment process is imported reagent simultaneously, and price is more expensive
Taking into account the high production cost of this method, it is also not suitable for large-scale production

Method used

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  • Preparation method for synthesizing intermediate compound of rosuvastatin calcium
  • Preparation method for synthesizing intermediate compound of rosuvastatin calcium
  • Preparation method for synthesizing intermediate compound of rosuvastatin calcium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 500mL three-necked flask equipped with a thermometer and a spherical condenser, add 20.0g (57.01mmol) of N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl ]-N-methylmethanesulfonamide and 30.6g (57.10mmol, 1.0eq) of (3R)-3-(tert-butyldimethylsilyl)oxy-5-carbonyl-6-triphenylphosphine ylide hexanoic acid Methyl ester, N 2 Under protection, 300 mL of acetonitrile was added, and the temperature was raised to 90°C. After stirring under reflux for 24 hours, the temperature was lowered to room temperature, and the acetonitrile was spin-dried under reduced pressure to obtain a crude product.

[0020] Add 80mL of methyl tert-butyl ether, 240mL of n-hexane, 160mL of ethanol, and 160mL of water into the crude product, stir thoroughly for 5 minutes, and separate the liquids (the upper layer is the organic phase, and the lower layer is the aqueous phase). Then add 160mL ethanol and 160mL water into the organic phase, fully stir for 5 minutes, separate the liquid (the u...

Embodiment 2

[0024] In a 500mL three-necked flask equipped with a thermometer and a spherical condenser, add 20.0g (57.01mmol) of N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl ]-N-methylmethanesulfonamide and 33.7g (62.8mmol, 1.1eq) of (3R)-3-(tert-butyldimethylsilyl)oxy-5-carbonyl-6-triphenylphosphine ylide hexanoic acid Methyl ester, N 2 Under protection, 300 mL of acetonitrile was added, and the temperature was raised to 90°C. After stirring under reflux for 24 hours, the temperature was lowered to room temperature, and the acetonitrile was spin-dried under reduced pressure to obtain a crude product.

[0025] Add 80mL of methyl tert-butyl ether, 240mL of n-hexane, 160mL of ethanol, and 160mL of water into the crude product, stir thoroughly for 5 minutes, and separate the liquids (the upper layer is the organic phase, and the lower layer is the aqueous phase). Then add 160mL ethanol and 160mL water into the organic phase, fully stir for 5 minutes, separate the liquid (the up...

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Abstract

The invention provides a preparation method for synthesizing intermediate compound of rosuvastatin calcium, which relates to a technique for synthesizing intermediate compound of Rosuvastatin Calcium. The intermediate compound is (R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino) pyrimidin-5-yl]-3-(tert-butyl dimethyl silicon)oxy-5-carbonyl-6(E)-methyl heptene. The method uses N-[4-(4-fluorophenyl)-5-formoxyl-6-isopropyl pyridine-2-yl]-N-methyl sulfonamide and (3R)-3-(tertiary butyl dimethyl silicon)oxy-5-carbonyl-6-triphenylphosphine ylide methyl caproate as raw material, through Wittig reaction, crude product is produced, and then, the crude product is separated and purified by phase disengagement, adsorption and other postprocessing methods, furthermore, the intermediate compound is (R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino) pyrimidin-5-yl]-3-(tert-butyl dimethyl silicon)oxy-5-carbonyl-6(E)-methyl heptene for synthesizing Rosuvastatin Calcium is obtained. The invention has the advantages of low cost, simple operation and good economic benefit, which is suitable for industrial production. The intermediate compound obtained by method provided by the invention can be used for preparing Rosuvastatin Calcium.

Description

technical field [0001] The invention discloses a method for preparing an intermediate for synthesizing rosuvastatin calcium, relating to a process for synthesizing an intermediate for rosuvastatin calcium. This intermediate is (R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3 -(tert-Butyldimethylsilyl)oxy-5-carbonyl-6(E)-heptenoic acid methyl ester. It belongs to the technical field of pharmaceutical synthesis and chemical engineering. Background technique [0002] Rosuvastatin Calcium is (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl ]-(3R,5S)-3,5-dihydroxyhept-6-enoic acid calcium salt, its structure is: [0003] [0004] Rosuvastatin calcium is a new type of HMG-CoA reductase inhibitor and a drug that can effectively reduce blood lipids. Because it has the advantages of high efficiency and low toxicity and side effects, and is currently the best curative effect among statin drugs, it is fa...

Claims

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Application Information

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IPC IPC(8): C07F7/18
Inventor 胡文浩厉铭陈雄杨琍苹
Owner 安徽美诺华药物化学有限公司
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