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Treatment method of by-product after enzymatic resolution of gamma-lactam

A technology of enzymatic splitting and treatment methods, applied in chemical instruments and methods, preparation of organic compounds, cyanide reaction preparation, etc., can solve the problems of increasing production cost and environmental protection pressure of production enterprises, and can only be discarded if there is no use value , to achieve the effect of increasing the use value

Inactive Publication Date: 2021-02-09
SHANGHAI SHYNDEC PHARMA HAIMEN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The by-product (+) 1-amino-4-formyl-2-cyclopentene has no use value and can only be discarded, increasing the production cost and the environmental protection pressure of the production enterprise

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 50 g of the by-product (+) 1-amino-4-formyl-2-cyclopentene after resolution and extraction by γ-lactam enzymatic method into a flask, add 200 g of water, and slowly add it dropwise at 25~30°C Sulfuric acid, adjust the pH value of the solution to 1~2. After the dropwise addition is completed, add 0.1 g of the racemization catalyst o-phthalaldehyde, then heat up to reflux, and react for 10~15 hours. Concentrate under reduced pressure until there is no distillate, add 200ml of methanol and 20g of tartaric acid, cool to 10~20°C, filter and wash with methanol. Add 20g of thionyl chloride and 100ml of methanol to the filter cake, react at 65°C for 8h, concentrate under reduced pressure until there is no distillate, add 100ml of dichloromethane, stir and dissolve, and wash the dichloromethane layer twice with drinking water to obtain (- ) 1-amino-4-formyl methyl-2-cyclopentene dichloromethane solution, yield 42%.

Embodiment 2

[0025] Weigh 50 g of the by-product (+) 1-amino-4-formyl-2-cyclopentene after resolution and extraction by γ-lactam enzymatic method into a flask, add 200 g of water, and slowly add it dropwise at 25~30°C Sulfuric acid, adjust the pH value of the solution to 2~3, after the dropwise addition is completed, add 0.1 g of the racemization catalyst o-phthalaldehyde, heat up to reflux, and react for 10~15 hours. Concentrate under reduced pressure until there is no distillate, add 200ml of methanol, 20g of tartaric acid, cool to 10-20°C, filter and wash with methanol. Add 20g of thionyl chloride and 100ml of methanol to the filter cake, react at 65°C for 8h, concentrate under reduced pressure until there is no distillate, add 100ml of dichloromethane, stir and dissolve, and wash the dichloromethane layer twice with drinking water to obtain (-) 1-Amino-4-methylcarboxylate-2-cyclopentene dichloromethane solution, yield 43.4%.

Embodiment 3

[0027] Weigh 50 g of the by-product (+) 1-amino-4-formyl-2-cyclopentene after resolution and extraction by γ-lactam enzymatic method into a flask, add 200 g of water, and slowly add it dropwise at 25~30°C Sulfuric acid, adjust the pH value of the solution to 3~4, after the dropwise addition is completed, add 0.1 g of the racemization catalyst o-phthalaldehyde, heat up to reflux, and react for 10-15 hours. Concentrate under reduced pressure until there is no distillate, add methanol 200ml, tartaric acid 20g, cool to 10~20°C, filter and wash with methanol. Add 20g of thionyl chloride and 100ml of methanol to the filter cake, react at 65°C for 8h, concentrate under reduced pressure until there is no distillate, add 100ml of dichloromethane, stir and dissolve, and wash the dichloromethane layer twice with drinking water to obtain (-) 1-Amino-4-methylcarboxylate-2-cyclopentene dichloromethane solution, yield 41.5%.

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PUM

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Abstract

The invention provides a treatment method of a by-product after enzymatic resolution of gamma-lactam. The treatment method comprises the following steps of carrying out racemization catalytic reactionon the by-product (+)1-amino-4-formate-2-cyclopentene, then adding methanol, tartaric acid, thionyl chloride and methanol, carrying out a reaction at 65 DEG C, then carrying out vacuum concentrationuntil no fraction exists, adding dichloromethane and water, carrying out stirring for dissolving, then carrying out standing for layering, and washing the separated dichloromethane layer with drinkingwater so as to finally prepare the (-)1-amino-4-methyl formate-2-cyclopentene dichloromethane solution. The method has the beneficial effects that the (-)1-amino-4-formate-2-cyclopentene dichloromethane solution prepared by the method is esterified to obtain the abacavir key intermediate (-)1-amino-4-methyl formate-2-cyclopentene, so that the use value is greatly improved.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a treatment method for by-products after enzymatic resolution of gamma-lactams. Background technique [0002] Abacavir sulfate is the sulfate salt of the antiviral drug abacavir. Its pharmacological action is the same as that of abacavir. It was successfully developed by Glaxo-Wellcome in the United Kingdom. Food and Drug Administration (FDA) approved marketing, trade name Ziagen, this product is a nucleoside reverse transcriptase inhibitor (NRTI), by inhibiting HIV reverse transcriptase, causing chain scission, preventing virus replication and effective. Studies have shown that this product is effective in combination with other nucleoside reverse transcriptase inhibitors such as didanosine, zalcitabine, lamivudine and stavudine. additive effect. It has a synergistic effect when used in combination with zidovudine. This provides a new triple therapy approach for the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C227/44C07C229/48
CPCC07C227/18C07C227/44C07C2601/10C07C229/48
Inventor 昝日虎路锐顾凯伟卢方洲白晶闫俊张跃敏
Owner SHANGHAI SHYNDEC PHARMA HAIMEN CO LTD
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