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Preparation method of 3, 5-dihydroxy heptyl-6-gadoleic acid derivative

A dimethyl propyl and benzyl technology, applied in the field of preparation of rosuvastatin calcium, can solve the problems of low total yield, high cost, low purity of rosuvastatin calcium, etc.

Active Publication Date: 2009-12-02
CHANGZHOU PHARMA FACTORY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0032] Although the patent EP0521471 discloses the synthesis method of rosuvastatin calcium, the applicant synthesizes it according to the patent method, and the obtained rosuvastatin calcium has low purity, low total yield and high cost

Method used

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  • Preparation method of 3, 5-dihydroxy heptyl-6-gadoleic acid derivative
  • Preparation method of 3, 5-dihydroxy heptyl-6-gadoleic acid derivative
  • Preparation method of 3, 5-dihydroxy heptyl-6-gadoleic acid derivative

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Embodiment

[0098] 1. Restore

[0099]

[0100]Add 300 mL of anhydrous THF and 85 mL of anhydrous methanol into a 500 mL dry reaction flask, add 6.3 g of TP-13, replace the reaction system with nitrogen, and stir until TP-13 is completely dissolved. Cool down to -80~-85°C with liquid nitrogen, add 12.8 mL of 1M diethylmethoxyborane tetrahydrofuran solution dropwise, control the rate of addition to keep the temperature between -80~-85°C, and drop it in about 30 minutes. Maintain the temperature at -80 to -85°C and continue stirring for 55 to 60 minutes. Then add 0.7g of sodium borohydride evenly in batches, and after about 80 to 90 minutes, maintain the temperature at -80 to -85°C. This process takes about 5.5 to 6 hours, and the reaction ends. Raise the temperature to 20-30°C within 2 hours, continue the heat preservation reaction for 2-3 hours, add 1.2g of glacial acetic acid, and distill under reduced pressure at 45-55°C to remove the methanol-tetrahydrofuran mixed organic solvent. ...

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Abstract

The invention improves a preparation method of 3, 5-dihydroxy heptyl-6-gadoleic acid derivative. Asymmetric reduction is performed on intermediate 3-hydroxy-5-oxo-6-heptenoic acid ester derivative, alkali hydrolysis is performed on the obtained 3, 5-dihydroxy heptyl-6-heptenoic acid ester derivative crude product which is treated by alkali hydrolysis to obtain 3, 5-dihydroxy heptyl-6-gadoleic acid sodium salt derivative which is extracted and purified to obtain 3, 5-dihydroxy heptyl-6-gadoleic acid sodium salt derivative solution, then 3, 5-dihydroxy heptyl-6-gadoleic acid sodium salt derivative is converted into 3, 5-dihydroxy heptyl-6-gadoleic acid derivative, and 3, 5-dihydroxy heptyl-6-gadoleic acid sodium salt derivative is again converted into 3, 5-dihydroxy heptyl-6-gadoleic acid ester derivative with high yield, and purification methods such as recrystallization are performed to obtain purified 3, 5-dihydroxy heptyl-6-gadoleic acid ester derivative. The purified 3, 5-dihydroxy heptyl-6-gadoleic acid ester derivative is then hydrolyzed into 3, 5-dihydroxy heptyl-6-gadoleic acid sodium salt derivative which is finally converted into 3, 5-dihydroxy heptyl-6-gadoleic acid calcium salt derivative. 3, 5-dihydroxy heptyl-6-gadoleic acid derivative with high quality is obtained.

Description

technical field [0001] The invention relates to a preparation method of rosuvastatin calcium. Based on the synthesis method provided by EP0521471, the present invention synthesizes rosuvastatin ester through the improvement of asymmetric reduction, hydrolyzes the ester to prepare rosuvastatin free acid, obtains rosuvastatin sodium salt solution through purification, and then converts the sodium salt For rosuvastatin acid, the initially purified rosuvastatin acid is converted into rosuvastatin ester at high yield again, and pure rosuvastatin ester is obtained by purification methods such as recrystallization. The pure rosuvastatin ester is then hydrolyzed into rosuvastatin sodium salt, and finally converted into rosuvastatin calcium salt. The preparation method of rosuvastatin calcium provided by the present invention not only has high yield, low cost and high quality, but also eliminates the need for column chromatography and other difficult large-scale manufacturing operatio...

Claims

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Application Information

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IPC IPC(8): C07D239/42A61P9/12A61P9/10
Inventor 陈本顺王兵邹林
Owner CHANGZHOU PHARMA FACTORY
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