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Preparation method of intermediate of rosuvastatin calcium side chain

A technology for rosuvastatin and intermediates, which is applied in the field of preparation of rosuvastatin calcium side chain intermediates, can solve the problems of difficult large-scale production, harsh process conditions, and low total yield, and achieve low cost and post-processing Ease of handling and high chiral purity

Active Publication Date: 2011-09-14
JIANGSU ALPHA PHARM CO LTD
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Problems solved by technology

[0010] The above method has a long route, low total yield, relatively harsh process conditions, and is not easy for large-scale production

Method used

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  • Preparation method of intermediate of rosuvastatin calcium side chain
  • Preparation method of intermediate of rosuvastatin calcium side chain
  • Preparation method of intermediate of rosuvastatin calcium side chain

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Embodiment Construction

[0022] The enzyme involved in the present invention comes from Jiangsu Alpha Pharmaceutical Co., Ltd.

[0023] Add 300 ml of dichloromethane at room temperature, stir and dissolve 120 g of imidazole, add dropwise tert-butyldimethylsilyl chloride solution (151 g dissolved in 600 ml of dichloromethane), add (R)-4-cyano-3- 150 grams of methyl hydroxybutyrate solution, after reacting for 16 hours at 20-25 ° C, washed twice with 500 milliliters (250 milliliters × 2) of water, and then washed with 400 milliliters of saturated sodium chloride solution until neutral. The solvent was distilled off to obtain 250 g of methyl (R)-4-cyano-3-tert-butyldimethylsilyloxybutyrate (II). (content 98%; yield is 98%)

[0024] In a stirred 1000 ml four-necked flask equipped with a thermometer, a pH meter and a dropping funnel, add (R)-methyl 4-cyano-3-tert-butyldimethylsilyloxybutyrate (II ) 50 grams (98.5%), 500 grams of water, 10 grams of liquid nitrilase, after adding, control the temperature i...

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Abstract

The invention discloses a preparation method of an intermediate of a rosuvastatin calcium side chain, which comprises the following steps: firstly allowing (R)-4-cyano-3- methyl hydroxybutyrate to react with tert-butyl-dimethylchlorosilane, performing nitrile group hydrolysis in water phase under the action of an enzyme with the obtained (R)-4-cyano-3-tert-butyl dimethylsiloxyl methyl butyrate (II) as a substrate to generate a target product with a structure (I). The invention has the characteristics of being mild in reaction, high in yield, environment friendly, low in cost, and high in chiral purity of the prepared product.

Description

technical field [0001] The invention relates to a preparation method of a rosuvastatin calcium side chain intermediate. Background technique [0002] Rosuvastatin calcium, whose chemical name is (+)-(3R,5S)-bis{7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N -methylsulfonamido)pyrimidine-5-]-3,5-dihydroxy-6-(E)-heptenoic acid} hemicalcium salt, is a new generation of HMG-COA reductase inhibitors, belonging to statins, It can treat hypercholesterolemia, mixed dyslipidemia and simple hyperlipidemia and triglycerides. Judging from its existing clinical verification results and comparison with similar products, risuvastatin is worthy of being called a "super statin", and its lipid-lowering effect is significantly better than similar lipid-lowering drugs. [0003] (R)-3-tert-butyldimethylsiloxyglutaric acid monomethyl ester (I) is an important intermediate in the synthesis of rosuvastatin calcium side chain. [0004] [0005] In recent years, this intermediate has received ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/62
Inventor 石振祥尹晓龙徐春涛
Owner JIANGSU ALPHA PHARM CO LTD
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