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Preparation method of R-type chiral sulfoxide compound

A compound and sulfoxide technology, applied in the field of preparation of R-type chiral sulfoxide compounds, can solve the problem of difficulty in separation, low content, affecting S-type ticagrelor sulfoxide or R-type ticagrelor sulfoxide process and other issues, to achieve the effect of mild reaction conditions

Inactive Publication Date: 2020-02-04
ZHUZHOU QIANJIN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the content of such impurities is very low during the synthesis of ticagrelor, and it is difficult to separate, which greatly affects the progress of S-type ticagrelor sulfoxide or R-type ticagrelor sulfoxide in biological activity research.

Method used

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  • Preparation method of R-type chiral sulfoxide compound
  • Preparation method of R-type chiral sulfoxide compound
  • Preparation method of R-type chiral sulfoxide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 A kind of R-type chiral sulfoxide compound

[0050] The R-type chiral sulfoxide compound was prepared and separated by the following method:

[0051](1) Dissolve 15.00g (35.80mmol) of compound I in 300mL of glacial acetic acid, add 120mL of deionized water to dilute, cool down to 4°C in an ice-salt bath, slowly add 25mL of sodium nitrite aqueous solution (containing 3.71g of sodium nitrite , 53.77mmol), heated to 30°C after dropping, reacted for 2.5h, added potassium carbonate to adjust the pH to neutral, extracted 3 times with 600mL ethyl acetate, combined organic layers, washed with saturated sodium chloride, dried and concentrated , to obtain 14.50g of compound II, yield 94.20%, purity 99.37%, ESI (m / z) [M-H] - :430.09;

[0052] (2) Dissolve 14.50g (33.73mmol) of compound II and 13.01g (1.2mmol) of compound III obtained in step (1) in 100mL of toluene, add 13.98g of potassium carbonate, stir and react at 30°C for 24h, concentrate under reduced pressure, a...

Embodiment 2

[0055] Example 2 A kind of R-type chiral sulfoxide compound

[0056] The difference from Example 1 is that the chiral reagent in Example 2 is S-mandelic acid, the oxidant is cumene hydroperoxide, and the remaining parameters and operations refer to Example 1 to obtain compound VI with a yield of 66.8% and a purity of 99.68%. %.

Embodiment 3

[0057] Example 3 A kind of R-type chiral sulfoxide compound

[0058] The difference from Example 1 is that the chiral reagent in Example 3 is (S,S)-1,2-diphenylethylene glycol, the oxidizing agent is hydrogen peroxide, and the remaining parameters and operations refer to Example 1 to obtain Compound VI, yield 67.54%, purity 99.75%.

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of an R-type chiral sulfoxide compound. The preparation method mainly comprises the four steps of ring formation, substitution, catalytic oxidation and hydrolysis to remove isopropylidene, a certain catalyst and a catalytic system which includes a metallic organic catalyst, a chiral reagent and water are adopted to be matched for a catalytic oxidation reaction, by combining a certain reaction sequence, the synthetic high-purity R-type chiral sulfoxide compound can be obtained, reaction conditions are mild, under the optimization condition, the high-purity R-type chiral sulfoxide compound can be further obtained with the high yield, and subsequent research for the bioactivity of the R-type chiral sulfoxide compound is facilitated.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis. More specifically, it relates to a preparation method of R-type chiral sulfoxide compounds. Background technique [0002] Ticagrelor is a new type of selective small molecule anticoagulant drug developed by AstraZeneca. The drug can reversibly act on the P2 receptor subtype P2Y12 on vascular smooth muscle cells, and has a significant inhibitory effect on platelet aggregation caused by ADP. It acts rapidly after oral administration, and can effectively improve the symptoms of patients with polar coronary heart disease. Moreover, the antiplatelet effect of ticagrelor is reversible, which is especially suitable for patients who need anticoagulant therapy before surgery. Compared with the similar drug clopidogrel, ticagrelor can significantly reduce the incidence of death from vascular causes, myocardial infarction or stroke, thereby reducing the incidence of thrombotic cardiovascular ev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07B2200/07C07D487/04
Inventor 袁红波文峰球杨丽芳王雪姣金秉德刘舞扬
Owner ZHUZHOU QIANJIN PHARMA
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