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A compound and organic solvent technology, applied in the field of preparation of temsirolimus, can solve the problems of highly toxic compounds, high price, and non-compliance with environmental protection and safety requirements, and achieve the effects of low cost, short preparation route and simple operation
Active Publication Date: 2012-11-28
SHANGHAI SHYNDEC PHARMA CO LTD
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[0011] The disadvantage of this synthetic route is that the reaction needs to use phenylboronic acid, which is ex
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[0028] Example 1
[0029] Add 2,2-bis(hydroxymethyl)propionic acid (5.00g, 37.28mmol) and triethylamine (26.41g, 0.26mol) into 50.00ml N,N-dimethylformamide, ice water bath, stir and add Tert-butyldimethylchlorosilane (19.60g, 0.13mol) was heated to room temperature and reacted for 5-8h to obtain 10.0g of compound Ⅰ-1.
[0033] Compound I-1 (5.00g, 13.79mmol) and triethylamine (2.10g, 20.75mmol) were added to 50.00ml of dichloromethane, stirred and added 2,4,6-trichlorobenzoyl chloride (3.30g, 13.53) mmol), after 6 hours of reaction at room temperature, slowly drip into 10.00ml dichloromethane containing rapamycin (4.20g, 4.60mmol) and 4-(N,N-dimethylamino)pyridine (2.25g, 18.38mmol) , And control the reaction temperature to 0°C~5°C, and obtain compound B-1 (3.47g) after 12 hours of reaction.
[0038] Compound B-1 (1.00 g, 0.79 mmol) was added to a solvent containing 15.00 ml of acetone, stirred and 1N hydrochloric acid (2.38 ml) was added in an ice-water bath to react for 1 to 2 hours to obtain tamsilimus (0.75 g).
[0039] MS: 1052.89 (M+23), 1 HNMR is the same as the product described in Example 11 in US5362718.
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Abstract
The invention belongs to the technical field of methods for preparing temsirolimus, and relates to a method for preparing temsirolimus. The method comprises the following steps of: 1) adding 2,2-bis(hydroxymethyl) propionic acid, organic alkali and chlorosilane into an organic solvent, and reacting to obtain a compound I; 2) dissolving the compound I and the alkali in the organic solvent, adding 2,4,6-trichlorobenzene formyl chloride, reacting, adding reaction liquid into an organic solvent of a compound A and 4-(N,N-dimethylamino) pyridine, and reacting to generate a compound B; and 3) reacting the compound B and acid to obtain the temsirolimus. Compared with the prior art, the method has the advantages of short preparation route, high yield, simplicity of operation and low cost, and is suitable for industrial production.
Description
technical field [0001] The invention belongs to the technical field of preparation methods of temsirolimus. Background technique [0002] Temsirolimus (CCI-779) is the first mTOR inhibitor drug product to be applied for the treatment of cancer, and it is suitable for the treatment of advanced renal cell carcinoma. Temsirolimus is approved as a first-line treatment for patients with advanced renal cell carcinoma who have failed initial therapy, and as a first-line and second-line treatment for metastatic primary renal cell carcinoma (RCC). The results of its phase III clinical trial showed that compared with α-interferon (the current conventional drug for the treatment of renal cell carcinoma) therapy, temsirolimus can prolong the median survival time by 3-6 months (increased by 50%), and its Drugs that can significantly prolong the survival of cancer patients. Studies have also shown that temsirolimus has a significant effect on the treatment of relapsed mantle cell lympho...
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