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Penicillin G sulfoxide diphenyl methyl ester synthesis method

A technology of diphenylmethyl sulfoxide and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of peracetic acid flammability, low safety factor, unfavorable operation, etc., achieve effective non-chlorine oxidation ability, high safety factor, easy The effect of the operation

Active Publication Date: 2020-02-28
YANCHENG KAIYUAN MEDICINE CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are two main aspects to the research on the oxidation process of penicillin G sulfoxide benzhydryl ester. One is to adopt the peracetic acid method, which has a high yield, but produces a large amount of acidic waste water, and the pollution is relatively serious, and the synthesis of peracetic acid belongs to High-risk process, peracetic acid is flammable, explosive, highly corrosive, and highly irritating, which is not conducive to operation and has a low safety factor; the second is to use hydrogen peroxide and supported catalyst oxidation method, which has low yield

Method used

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  • Penicillin G sulfoxide diphenyl methyl ester synthesis method
  • Penicillin G sulfoxide diphenyl methyl ester synthesis method
  • Penicillin G sulfoxide diphenyl methyl ester synthesis method

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Embodiment 1

[0028] (1) Synthesis of compound 2:

[0029] Add 120ml of dichloromethane, diphenylmethanol (23.2g, 0.126mol) and compound 1 (40g, 0.107mol) to a 500ml four-neck flask, cool down to 15°C, add pyridine (16g, 0.202mol), and control the temperature for 10-15°C. Add methanesulfonyl chloride (16 g, 0.140 mol) dropwise at ℃ for 60 minutes, and keep warm for 4 hours after dropping. At the end of the heat preservation, 135 g of 5% dilute sulfuric acid was added for washing, the organic phase was separated, the aqueous phase was extracted with 30 ml of dichloromethane, and the organic phases were combined to obtain a dichloromethane solution of compound 2, which was then transferred to a 1000 ml four-necked bottle for use.

[0030] (2) Synthesis of compound 3:

[0031] Adjust the temperature of the dichloromethane solution of compound 2 prepared in the previous step to 22°C. Preparation of potassium persulfate complex salt solution: weigh potassium persulfate complex salt (45 g, 0.07...

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Abstract

The invention discloses a penicillin G sulfoxide diphenyl methyl ester synthesis method, which comprises: esterifying a penicillin G potassium salt as an initial raw material, and oxidizing through 2KHSO5.KHSO4.K2SO4 to synthesize the penicillin G sulfoxide diphenyl methyl ester. According to the invention, the product purity is more than 99%, the total molar yield is more than 95%, the method issuitable for industrial production, and the method has advantages of readily available raw materials, high yield, less pollution, high safety factor, easy operation and the like.

Description

technical field [0001] The invention belongs to the field of synthesis of small molecular compounds, and relates to a synthesis method of penicillin G sulfoxide benzhydryl ester. Background technique [0002] Cephalosporins are an important class of antibiotics, which have strong antibacterial effect, good curative effect, low toxicity, and dual characteristics of broad-spectrum and penicillinase resistance. Therefore, it has a bright prospect as a clinical first-line drug. At present, cephalosporins and their intermediates such as 7-AVCA, 7-ACCA, 7-ANCA and 7-AMCA are mainly prepared from 7-ACA and penicillin. However, due to the high cost of preparation of 7-ACA as a raw material [1], many people turned their attention to the raw material of penicillin, which has a wide source and relatively cheap price. Penicillin G sulfoxide benzhydryl ester is an important intermediate in the synthesis of cephalosporins through ring expansion, so the study on its synthesis process is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/46C07D499/04
CPCC07D499/46C07D499/04
Inventor 邱国华陈迪才汪前胜王红萍
Owner YANCHENG KAIYUAN MEDICINE CHEM
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