Synthesizing method of N-methoxyphenyl-N-(acetyl)methylamine

The technology of a methoxyphenyl group and a synthetic method, which is applied in the field of pharmaceutical intermediate synthesis, can solve the problems of complicated process, solvent toxicity, unsuitability for industrial production and the like, and achieves the effect of simple process and simple process.

Inactive Publication Date: 2012-06-13
SHANGHAI NEW ASIA PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The object of the present invention is to provide a synthetic method for the intermediate N-methoxyphenyl-N-(acetyl)methylamine for the synthesis of 4-AA. Solve the problem that in the existing technology of

Method used

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  • Synthesizing method of N-methoxyphenyl-N-(acetyl)methylamine
  • Synthesizing method of N-methoxyphenyl-N-(acetyl)methylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0035] A kind of synthesis technique of 4-acetoxy azetidinone intermediate is carried out according to the following steps:

[0036]Add 102g (0.83mol) of p-aminoanisole, 184g of ethyl acetate, and 122g of triethylamine into a 1000mL four-necked bottle, stir while heating up in a water bath, when the internal temperature rises to 65°C, keep the constant temperature, and use a funnel to Quickly add 92.5g (1 mol) of chloroacetone, keep reflux for 30min, then add 305g of water to terminate the reaction.

[0037] After static separation, the lower aqueous phase was discarded, 305g of petroleum ether was added to the organic phase, placed in a low-temperature water tank, cooled to -10°C, and stirred for 1 to 2 hours to grow crystals.

[0038] After suction filtration, the filter cake was rinsed with 10 g of petroleum ether, then with 30 g of water, and filtered to dryness by suction to obtain a light yellow crystal of N-methoxyphenyl-N-(acetyl)methylamine.

[0039] The product yiel...

Embodiment 2

[0041] A kind of synthesis technique of 4-acetoxy azetidinone intermediate is carried out according to the following steps:

[0042] Add 102g (0.83 mol) of p-aminoanisole, 184g of ethyl acetate, and 122g of triethylamine into a 1000mL four-necked bottle, stir while heating up in a water bath, when the internal temperature rises to 65°C, keep the constant temperature, slowly Add 92.5g (1 mol) of chloroacetone, dropwise within 30min, keep warm and reflux for 30min, add 305g of water to terminate the reaction.

[0043] After static separation, the lower aqueous phase was discarded, 305g of petroleum ether was added to the organic phase, placed in a low-temperature water tank, cooled to -10°C, and stirred for 1 to 2 hours to grow crystals.

[0044] After suction filtration, the filter cake was rinsed with 10 g of petroleum ether, then with 30 g of water, and filtered to dryness by suction to obtain a light yellow crystal of N-methoxyphenyl-N-(acetyl)methylamine.

[0045] The prod...

Embodiment 3

[0047] A kind of synthesis technique of 4-acetoxy azetidinone intermediate is carried out according to the following steps:

[0048] Add 148g (1.2mol) of p-aminoanisole, 197g of ethyl acetate, and 99g of triethylamine into a 1000mL four-necked bottle, stir while heating up in a water bath, when the internal temperature rises to 85°C, keep the constant temperature, slowly Add 100g (1.08mol) of chloroacetone, dropwise within 40min, keep warm and reflux for 60min, add 296g of water to terminate the reaction.

[0049] After static separation, the lower aqueous phase was discarded, 592g of petroleum ether was added to the organic phase, placed in a low-temperature water tank, the temperature was lowered to 0°C, and the crystal was grown by stirring for 1-2 hours.

[0050] After suction filtration, the filter cake was rinsed with 15g of petroleum ether, then with 45g of water, and filtered to dryness by suction to obtain a light yellow crystal of N-methoxyphenyl-N-(acetyl)methylamin...

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Abstract

The invention relates to a synthesizing method of N-methoxyphenyl-N-(acetyl)methylamine. According to the invention, para-anisidine and chloroacetone are adopted as raw materials. The method comprises steps that: 1, para-anisidine, and ethyl acetate and triethylamine used as reaction solvents are added into a reaction vessel, wherein a dosage amount of the reaction solvents is 2-4 times that of para-anisidine; the mixture is heated while stirring; chloroacetone is added to the mixture when the temperature is 65-85 DEG C; the mixture is then subject to a reaction with maintained temperature for 30-60min; a proper amount of water is added to the reaction vessel to stop the reaction; 2, the obtained mixture is settled and layered; a lower-layer water phase is removed; ligroin is added to an organic phase, and the mixture is stirred for 1-2h, such that crystals can grow; 3, the mixture is subject to pump filtration, a filter cake is leached by using ligroin and then leached by using water; the filter cake is dried by pump filtration, such that light yellow crystals, which are N-methoxyphenyl-N-(acetyl)methylamine products, are obtained. According to the method provided by the invention, the solvents are advantaged in low toxicity and easy recycling. The technical processes of the method are simple, and the method is suitable for industrialized productions. With the method, a molar yield is higher than 75%. As a result of HPLC detection, the purity of the product is higher than 93%.

Description

technical field [0001] The synthesis method of N-methoxyphenyl-N-(acetyl)methylamine of the present invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular a 4-acetoxy-3-[1-(tert-butyldi The synthetic method of the intermediate of methylsilyloxy group) ethyl] azetidinone. Background technique [0002] Many β-lactam antibiotics were developed in the 1960s to 1980s and continued to evolve with the emergence of antibiotic resistance. It is widely recognized for its high efficacy and low toxicity in treatment. And become the cornerstone of clinical treatment of bacterial infectious diseases. However, the widespread use in the past 50 years has resulted in the resistance of many clinically important bacteria to these lactam antibiotics. These resistance phenotypes have reduced the frequency of clinical use of β-lactam antibiotics. The persistent existence of this drug resistance problem has prompted the development of novel antibio...

Claims

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Application Information

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IPC IPC(8): C07C225/06C07C221/00
Inventor 郑玉林张道凌于永宏姜文婷刘明
Owner SHANGHAI NEW ASIA PHARMA
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