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Method for preparing DL-serine

A serine and hydrochloric acid technology, applied in the chemical industry, can solve the problems of difficult separation and purification of the final product, obvious amplification effect, low reaction yield, etc., and achieve the effects of high product yield, easy separation and operation, and good reproducibility

Inactive Publication Date: 2008-04-30
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Purpose of the invention: To provide a preparation method of DL-serine to overcome the deficiencies in the prior art such as low reaction yield, difficulty in separation and purification of the final product, obvious amplification effect, and poor reproducibility

Method used

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  • Method for preparing DL-serine
  • Method for preparing DL-serine

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add respectively 30ml absolute ethanol, 3.4g (0.05mol) methyleneamino acetonitrile, 1.8g (0.06mol) paraformaldehyde and 0.5g 4 -Dimethylaminopyridine (DMAP), raise the temperature under stirring and control the temperature at 55±5°C, slowly add 8.36ml (0.06mol) triethylamine dropwise, continue to react at 45±5°C for 4 hours after the drop, and use TLC Detection reaction end point (developing agent is V 石油醚 :V 乙酸乙酯 = 1: 1), after the reaction, adjust the pH of the solution with 5mol / l hydrochloric acid to be 7, then concentrate under reduced pressure to half of the original volume, reclaim 15ml of ethanol, leave it for 3 hours, and separate out 4.2g of white crystals, which is 1- Hydroxymethyl-1-methyleneaminoacetonitrile, m.p.64.0-64.5°C, yield 85.7%.

[0024] The above obtained 4.2g 1-hydroxymethyl-1-methyleneamino acetonitrile was added to 23ml of 10mol / l hydrochloric acid, heated under stirring, refluxed for 10 hours, and detected by TLC until the raw material poin...

Embodiment 2

[0026] Add 60ml absolute ethanol, 6.8g (0.10mol) methyleneamino acetonitrile, 3.6g (0.12mol) paraformaldehyde and 0.05g 4 - Dimethylaminopyridine (DMAP), raise the temperature under stirring and control the temperature at 55±5°C, slowly add 16.72ml (0.12mol) triethylamine dropwise, continue to react at 45±5°C for 5 hours after the drop, and use TLC Detection reaction end point (developing agent is V 石油醚 :V 乙酸乙酯 =1:1), after the reaction, adjust the pH of the solution to 7 with 5mol / l hydrochloric acid, then concentrate under reduced pressure to half of the original volume, reclaim 30ml of ethanol, leave it standing, and separate out 6.4g of white crystals, which is 1-hydroxymethyl Base-1-methyleneaminoacetonitrile, m.p.63-65°C, yield 65.3%.

[0027] The 6.4g 1-hydroxymethyl-1-methyleneamino acetonitrile obtained above was added in 23ml of 10mol / l hydrochloric acid, heated under stirring, refluxed for 12 hours, and detected by TLC until the raw material point disappeared (dev...

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Abstract

The invention discloses a preparation method of DL-serine. The invention adds methylamino methyl cyanide and paraformaldehyde into ethanol reaction solvent, and the addition reaction is performed with organic alkali triethylamine under the existence of catalytic agent, so as to obtain 1-methylol-1-methylamino methyl cyanide, and DL-serine of the invention is obtained through hydrochloric acid hydrolization; the yield rate is 86.7 to 88.9 percent, and the melting point is 245 DEG C (decomposition). Compared with the prior technology, the segregation operation of the invention is simple and convenient, the reactant raw material sources are extensive, the product yield rate is higher, the reproducibility is better, and the invention is suitable for the industrialized production.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a method for preparing DL-serine. Background technique [0002] DL-serine is an important organic chemical raw material, which can be further resolved to obtain two enantiomers L-serine and D-serine. L-serine is used to prepare serine compound infusion, or directly as the main raw material for enzymatically synthesizing L-tryptophan and other pharmaceutical intermediates. D-serine is used to synthesize D-cycloserine, a special drug for the treatment of tuberculosis, and can also be used as a preparation An important raw material for pharmaceutical intermediates. Its structural formula is: [0003] [0004] In the prior art, the research reports related to the preparation method of DL-serine are mainly as follows: Fine Chemical Industry, 18(4), 232-233 (2001) reported the preparation of DL-serine by copper glycine method. Glycine and copper sulfate form a complex under the a...

Claims

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Application Information

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IPC IPC(8): C07C229/22C07C227/12
Inventor 廖本仁袁振文
Owner SHANGHAI CHEM REAGENT RES INST
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