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The synthetic method of triptolide intermediate

A technology for intermediates and compounds, applied in the field of preparation of organic compounds, can solve the problems of low selectivity, insufficient stereoselectivity, long routes, etc., and achieve good stereoselectivity and yield, good non-corresponding selectivity, and good reaction mild conditions

Active Publication Date: 2016-08-17
甘肃皓天医药科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In 2009, the Chinese invention patent application CN101638426 disclosed a method for synthesizing compounds 3 and 4 with the alkylation of the ortho carbonyl group and the aldol condensation in the molecule as the key steps shown in formula 5. The method has a long route and the reaction conditions More complicated, and the stereoselectivity is not good enough
[0019] In view of the inefficiency, low selectivity, etc. Due to the good biological activity and great potential application value of natural products, it is of great significance to develop new and efficient asymmetric synthesis methods for compound 4, triptolide and triptolide

Method used

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  • The synthetic method of triptolide intermediate
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  • The synthetic method of triptolide intermediate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the reaction process is shown in formula 9, namely R in formula 7 1 , R 2 , R 3 and R 4 is methyl, R 5 is trifluoromethyl, that is, the base used for the conversion of compound 7a to compound 11a is triethylamine, the trialkylsilicon reagent is trimethylchlorosilane, and the catalytic hydrogenation catalyst used for the conversion of compound 11a to 12a is 5% Pd-C , the conversion of compound 12a to compound 13a is carried out under the action of tetrabutylammonium fluoride, the base used for the conversion of compound 13a to compound 14a is pyridine, the sulfonylation reagent is trifluoromethanesulfonic anhydride, and the reducing agent for reducing compound 14a It is diisobutylaluminum hydride, and the catalyst for the carbonyl insertion reaction of compound 15a is palladium acetate.

[0030] Formula 9

[0031] Preparation of compound 11a

[0032]In a 250 mL round-bottomed flask, compound 7a (6.28 g, 20 mmol) was dissolved in 100 mL of dry dic...

Embodiment 2

[0043] Embodiment 2: the reaction process is shown in formula 10, namely R in formula 7 1 is tert-butyl, R 2 , R 3 and R 4 is phenyl, R 5 For p-tolyl, that is, the base used to convert compound 7b to compound 11b is potassium carbonate, the trialkylsilicon reagent is triphenylchlorosilane, the catalytic hydrogenation catalyst used to convert compound 11b to 12b is Raney Ni, and compound 12b is converted to Compound 13b was carried out under the action of 2M hydrochloric acid, the base used for the conversion of compound 13b to compound 14b was triethylamine, the sulfonylation reagent was p-toluenesulfonyl chloride, the reducing agent for reducing compound 14b was sodium borohydride-iodine, and the compound The catalyst for the carbonyl insertion reaction of 15b is palladium chloride.

[0044] Formula 10

[0045] Preparation of compound 11b

[0046] In a 250 mL round-bottomed flask, compound 7b (6.5 g, 20 mmol) was dissolved in 100 mL of dry dichloromethane, potassiu...

Embodiment 3

[0057] Embodiment 3: Reaction process is shown in formula 11, namely R in formula 7 1 is n-butyl, R 2 is tert-butyl, R 3 and R 4 is methyl, R 5 The base used for the conversion of the p-methyl group, i.e., compound 7c to compound 11c, was imidazole, the trialkylsilicon reagent was tert-butyldimethylsilyl chloride, and the catalytic hydrogenation catalyst used for the conversion of compound 11c to 12c was PtO 2 , the conversion of compound 12c to compound 13c is carried out under the action of p-toluenesulfonic acid, the base used for the conversion of compound 13c to compound 14c is diisopropylethylamine, the sulfonylation reagent is methanesulfonyl chloride, and the reduction of compound 14c The reagent is sodium borohydride-boron trifluoride ether, and the catalyst for the carbonyl insertion reaction of compound 15c is diacetonitrile palladium dichloride.

[0058] Formula 11

[0059] Preparation of compound 11c

[0060] In a 250 mL round-bottomed flask, compound 7...

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Abstract

The invention discloses a preparation method of intermediate compounds for preparing triptolide compounds, triptonide compounds and triptophenolide compounds, and a series of new compounds produced in the preparation process with the preparation method. The compound provided by the invention is obtained by using the compound 7 represented by a formula as an initial raw material through the reaction process represented by the formula.

Description

technical field [0001] The present invention relates to a preparation method of an organic compound, specifically the present invention relates to an intermediate for preparing triptolide compound 1, triptolide compound 2 and triptolide compound 4 as shown in formula 1 The preparation method of compound 3, and a series of new compounds produced in the process of preparing compound 3 by this preparation method. [0002] [0003] Formula 1 Background technique [0004] Tripterygium wilfordii (Tripterygium wilfordii) is a plant of the family Euonymus. As a traditional Chinese medicine, it has a long history of being used in the treatment of various diseases. Compounds 1, 2 and 4 shown in the above formula, namely triptolide alcohol, triptolide and triptolide, are all diterpenoid lactone compounds isolated from triptolide plants. Studies in the past two decades have shown that they have various significant biological activities such as anti-inflammatory, immunosuppressive, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77C07C309/65C07F7/18
CPCY02P20/55
Inventor 薛吉军张虹锐李海峰李瀛高强郑保富
Owner 甘肃皓天医药科技有限责任公司
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