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Preparation method of compound

A technology of compounds and complexes, which is applied in the field of preparation of ferrocene compounds, can solve the problems of expensive phosphoramidites, difficult quality control, and low reaction yields, and achieve rapid reactions, low production costs, and reproducibility Good results

Active Publication Date: 2017-06-20
厦门云凡医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, this method disclosed in WO2009061941 has many disadvantages in reaction control, such as the key material 2-cyanoethyl N,N-diisopropyl phosphoramidite chloride is very expensive, and it is easy to mix with air in the storage process. The water reaction of N205 and N329 and 2-cyanoethyl N, N-diisopropyl phosphoramidite reaction yields are very low; when this route produces N330, there are many by-products; these factors As a result, the production cost of N330 is very high, and the quality is difficult to control

Method used

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Examples

Experimental program
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Embodiment 1

[0080]

[0081] AlCl 3 (17.70g, 132.8mmol), DCM (200.0mL) in 500mL inclined two-necked flask, N 2 Under protection, lower to 0°C, slowly add 3-chloropropionyl chloride (13.5mL, 141.6mmol) dropwise, and keep warm for 1h to obtain A solution;

[0082] Take DMF (80.0mL) in a 100mL eggplant bottle, add NaBH in batches 4 (6.10g, 161.2mmol), heated to 45°C and stirred for 3h to obtain B solution;

[0083] Get ferrocene (20.00g, 107.5mmol) and be dissolved in DCM (52.0mL), N 2 Under protection, solution A was slowly added dropwise at room temperature, after the dropwise addition was completed, the reaction was carried out at room temperature for 30 minutes; when the temperature was lowered to 0°C, solution B was slowly added dropwise, after the addition was completed, it was raised to room temperature for 1 hour reaction. Slowly add water (200.0mL) to quench the reaction, separate layers, extract the aqueous phase with DCM, wash with water; anhydrous Na 2 SO 4 After drying an...

Embodiment 2

[0087]

[0088] Take THF (356.0mL), II-1 (24.00g, 200.0mmol), TsOH (1.20g, 6.3mmol) in a 1L oblique two-necked flask, slowly add benzaldehyde (21.4mL, 210.0mmol), dropwise , Reaction at room temperature for 12h.

[0089] Adjust the pH to 7.0 with ammonia water, evaporate THF under reduced pressure; 2 SO 4 After drying and concentrating, 37.12 g of white solid compound II-2 was obtained, with a yield of 89.1%.

Embodiment 3

[0091]

[0092] N 2 Under protection, take compound II-2 (5.00g, 24.0mol), DCC (6.43g, 31.2mmol), DMAP (0.293g, 2.4mmol), DCM (48.0mL) in a 100mL oblique two-necked flask, and drop to 0 ℃; Slowly add levulinic acid (2.7mL, 26.4mmol) dropwise and keep warm for 1h. Filtration and concentration gave blood red oily compound II-3.

[0093] Add MeOH (33.0mL) to the flask containing compound II-3 to dissolve, then transfer to a 500mL inclined two-neck flask, then add hydrochloric acid (33.2mL, 4mol / L), and react at room temperature for 2h.

[0094] Adjust pH to 7.0 with NaOH solution (33.2mL, 4mol / L), distill off MeOH, extract with DCM (3×40mL), anhydrous Na 2 SO 4 Drying and concentration gave brownish-red oily compound II-4.

[0095] N 2 Under protection, add TEA (3.3mL, 23.9mmol), DMAP (0.265g, 2.2mmol), DCM (27.7mL) to the flask containing compound II-4; slowly drop DMTCl dissolved in DCM (27.7mL) (6.65g, 23.9mmol) solution, reacted overnight.

[0096] Water (1×50mL), 5...

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Abstract

The invention discloses a preparation method of a compound. The compound has a structure shown in the formula I. The preparation method comprises that a compound II and a compound III undergo a reaction to produce a solution of an intermediate IV under action of an acid / azole complex, a compound V is added into the solution of the intermediate IV, the mixture undergoes a reaction to produce a solution of an intermediate VI under action of an acid / azole complex, a butanone peroxide solution is slowly added into the solution of the intermediate VI so that a solution of an intermediate VII is obtained, a hydrazine acetate solution is slowly added into the solution of the intermediate VII so that a compound VIII is obtained, and the compound VIII and the compound III undergo a reaction under action of an acid / azole complex to produce a compound I.

Description

technical field [0001] The present invention relates to a method for preparing a compound, in particular to a method for preparing a compound, especially a method for preparing a ferrocene compound. Background technique [0002] WO2009061941 discloses a compound of structural formula I, which can be labeled on a DNA fragment as a DNA electrochemical probe. Compared with traditional methods (such as using radioactive isotopes, fluorescent molecules, chemiluminescent reagents, etc. to label DNA probes prepared), The electrochemical method has the characteristics of simple and cheap instrument operation, accurate and rapid determination, and high sensitivity of the method. [0003] [0004] WO2009061941 also describes a process for the preparation of the general formula N330 starting from the starting compound ferrocene derivatives, the general formula I comprising the compound N330: [0005] In this case, ferrocene is produced by 3-chloropropionyl chloride and aluminum tri...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 叶兆宝罗善梅翁善晖谢垠榕李科
Owner 厦门云凡医药科技有限公司
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