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Synthetic method of pyrone compounds

A synthesis method and compound technology, applied in the field of synthesis of pyrone compounds, can solve the problems of high cost, difficulty in scale-up, complex process route purification, etc., and achieve the effect of low cost, high conversion rate and low equipment requirements

Active Publication Date: 2018-03-09
RAFFLES PHAMRMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aiming at the deficiencies of the prior art, in order to improve the current synthesis of pyrone compounds, the purification process is complicated, the cost is high, and it is not easy to scale up. The present invention provides a synthetic method for pyrone compounds

Method used

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  • Synthetic method of pyrone compounds

Examples

Experimental program
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Embodiment 1

[0030] Synthesis of dimethyl 4-oxo-3-methoxy-4H-pyran-2,5-dicarboxylate

[0031]

[0032] Synthesis steps: Add 105ml of 1M lithium hexamethyldisilazide tetrahydrofuran solution into a three-necked flask, cool to -15°C under nitrogen protection, add 14.6g of methyl 4-methoxyacetoacetate dropwise while keeping warm, and then continue to drop 6.0g Methyl formate, after dropping, keep warm for 2h. Add 120ml of 1M lithium hexamethyldisilazide solution in tetrahydrofuran, then add 13.4g of dimethyl oxalate, raise the temperature to 20-25°C for 3h. The reaction solution was transferred to pre-cooled 300ml 2N hydrochloric acid, stirred at room temperature for 2 hours, concentrated to remove tetrahydrofuran, added ethyl acetate for extraction, the organic phase was washed with water, concentrated, and finally crystallized with isopropanol to obtain 4-oxo-3-methoxy- 16.5 g of dimethyl 4H-pyran-2,5-dicarboxylate, yield 68%.

Embodiment 2

[0034] Synthesis of Dimethyl 4-oxo-3-benzyloxy-4H-pyran-2,5-dicarboxylate

[0035]

[0036] Synthesis steps: Add 105ml of 1M tetrahydrofuran solution of lithium hexamethyldisilazide to a three-necked flask, cool to -15°C under nitrogen protection, add 22.2g of methyl 4-benzyloxyacetoacetate dropwise while keeping warm, and then continue to add 6.0 g methyl formate, after dropping, keep warm for 3h. Add 125ml of 1M tetrahydrofuran solution of lithium hexamethyldisilazide, and then add 13.6g of dimethyl oxalate, raise the temperature to 35-40°C for 3h. The reaction solution was transferred to pre-cooled 300ml 2N hydrochloric acid, stirred at room temperature for 2 hours, concentrated to remove tetrahydrofuran, added ethyl acetate for extraction, the organic phase was washed with water, concentrated, and finally crystallized with isopropanol to obtain 4-oxo-3-benzyloxy- 19.7 g of dimethyl 4H-pyran-2,5-dicarboxylate, yield 62%.

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Abstract

The invention discloses a synthetic method of pyrone compounds. The method comprises the following steps: S1, carrying out condensation on a compound 1 and a compound 2 by using a strong base, so as to obtain a separable intermediate 3; S2, carrying out condensation on the intermediate 3 and a compound 4 by using a strong base, so as to obtain an intermediate 5; and S3, carrying out cyclization onthe intermediate 5 with an acid, so as to obtain a pyrone compound 6. The synthesis route is simple in operation, the yield is larger than 60%, the conversion rate is high, and amplification is facilitated. The synthetic method has easily available raw materials in the process, has low cost, has no special operation procedures, is not high in requirement on equipment, is convenient to operate andcontrol, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to the field of organic chemical synthesis, more specifically, to a method for synthesizing pyrone compounds. Background technique [0002] At present, two anti-HIV drugs, Dolutegravir and Cabotegravir, contain pyridone fragments on the market, and pyridone can be obtained through the reaction of pyrone compounds and amino compounds. [0003] [0004] At present, there are two main synthetic routes for pyrone compounds, one of which uses N,N-dimethylformamide dimethyl acetal as the condensation reagent, and the route is shown in the following formula. The main drawback of this route is that the reagents are expensive, the yield is low, and the cost is high. [0005] [0006] Another synthetic method is the following synthetic route. This synthetic route is relatively better, and the reagent orthoformate compounds used are relatively cheap, and the reaction conditions are relatively mild. [0007] [0008] Howev...

Claims

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Application Information

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IPC IPC(8): C07D309/40
CPCC07D309/40
Inventor 费安杰叶伟平周章涛黄志宁傅利尹志媛
Owner RAFFLES PHAMRMATECH CO LTD