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Synthesis method of p-hydroxyphenylglycine methyl ester

A technology of p-hydroxyphenylglycine methyl ester and p-hydroxyphenylglycine, applied in chemical instruments and methods, preparation of organic compounds, chemical recovery, etc., can solve high raw material cost and transportation cost, unsuitable for commercial production, environmental protection pressure Large and other problems, to achieve the effect of low cost, less environmental pollution, and mild reaction conditions

Active Publication Date: 2012-10-10
SHANDONG HANXING PHARM TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] CN200880022901.3 discloses that p-hydroxyphenylglycine is reacted in the presence of concentrated hydrochloric acid and 2,2-dimethoxypropane to obtain p-hydroxyphenylglycine methyl ester, and the method adopts methylating reagent 2,2-dimethoxypropane Irritant, high cost of raw materials and transportation, not suitable for commercial production
[0007] In summary, there are defects such as high production cost, low yield, cumbersome operation, high pressure on environmental protection, and low yield in the prior art

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] According to p-hydroxyphenylglycine: methanol molar ratio is 1: 25, p-hydroxyphenylglycine: silicotungstic acid mass ratio is 1: 0.2, carry out following reaction:

[0030] Immerse activated carbon in a saturated aqueous solution of silicotungstic acid, stir for 10-12 hours, filter to obtain a wet product, and dry it at 110°C for later use.

[0031] Mix 50g of p-hydroxyphenylglycine and methanol, stir evenly, add 1 N hydrochloric acid, stir at room temperature for 0.5 hours, then add activated carbon-supported silicotungstic acid, heat up to 60-65°C for reaction, and detect the end of the reaction by TLC. After the reaction, cool down, remove silicotungstic acid by suction filtration, concentrate the filtrate under reduced pressure to remove excess methanol, add 200ml of water to dissolve the concentrate, neutralize with ammonia water to pH=7, filter, and dry to obtain 49g of p-hydroxyphenylglycine methyl ester. The yield is 90.5% (based on p-hydroxyphenylglycine), and ...

Embodiment 2

[0034] According to p-hydroxyphenylglycine: methanol mol ratio is 1: 50, p-hydroxyphenylglycine: phosphomolybdic acid mass ratio is 1: 1, carries out following reaction:

[0035] Activated carbon-supported phosphomolybdic acid was prepared as in Example 1 for subsequent use.

[0036] Mix 50g of p-hydroxyphenylglycine and methanol, stir evenly, add 1 equivalent of trifluoroacetic acid, stir at room temperature for 1 hour,

[0037] Add activated carbon-loaded phosphomolybdic acid, heat up to 75-80°C for reaction, and detect the end point of the reaction by TLC. After the reaction, cool down, remove phosphomolybdic acid by suction filtration, concentrate the filtrate under reduced pressure to remove excess methanol, add 200ml of water to dissolve the concentrate, neutralize it with aqueous sodium bicarbonate to pH=7.5, filter, and dry to obtain p-hydroxyphenylglycine methyl The ester was 51 g, the yield was 94.3% (based on p-hydroxyphenylglycine), and the HPLC purity was 99.5%. ...

Embodiment 3

[0039] According to p-hydroxyphenylglycine: methanol molar ratio is 1: 30, p-hydroxyphenylglycine: phosphotungstic acid mass ratio is 1: 0.8, carry out following reaction:

[0040] Activated carbon-supported phosphotungstic acid was prepared according to the method in Example 1 for future use.

[0041] Mix 50g of p-hydroxyphenylglycine and methanol, stir evenly, add 0.5 equivalent of sulfuric acid dropwise, stir at room temperature for 30 minutes, add activated carbon-loaded phosphotungstic acid, heat up to 50-55°C for reaction, and detect the end point of the reaction by TLC. After the reaction, cool down, remove phosphotungstic acid by suction filtration, concentrate under reduced pressure to remove excess methanol, dissolve the concentrated solution in 200ml of water, neutralize with aqueous sodium hydroxide solution to pH=8.5, filter with suction, and dry to obtain p-hydroxyphenylglycine methyl The ester was 50 g, the yield was 92.4% (based on p-hydroxyphenylglycine), and ...

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PUM

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Abstract

The invention discloses a synthesis method of p-hydroxyphenylglycine methyl ester. The method comprises the steps of: reacting p-hydroxyphenylglycine or salt thereof which is used as an initial raw material with methanol in the presence of solid acid; and treating so as to obtain p-hydroxyphenylglycine methyl ester. The preparation method of p-hydroxyphenylglycine methyl ester is available in raw material, simple and convenient to operate, low in cost, high in yield, high in product purity, and is suitable for commercial production.

Description

technical field [0001] The invention relates to the synthesis of a pharmaceutical intermediate, in particular to the synthesis of an antibiotic drug intermediate, and belongs to the field of pharmaceutical chemical industry. Background technique [0002] P-Hydroxyphenylglycine methyl ester is an important intermediate of antibiotics, which is used to synthesize the side chains of β-lactam semi-synthetic antibiotics. [0003] The prior art discloses the preparation of p-hydroxyphenylglycine methyl ester with p-hydroxyphenylglycine and methanol in the presence of thionyl chloride. This method produces a large amount of hydrogen chloride gas during the operation of thionyl chloride, which puts forward higher requirements on the corrosion resistance of equipment. , bringing certain pressure to environmental protection. [0004] Michele Penso et al. (European Journal of Organic Chemistry, (23), 2003) reported the esterification of p-hydroxyphenylglycine and anhydrous methanol in...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/18
CPCY02P20/582
Inventor 楼军军庄程翰申屠阳沈天丰靳小舜朱鹏肖智力
Owner SHANDONG HANXING PHARM TECH CO LTD
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