Synthesis method of (D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide

A kind of technology of dimethyl aziridine and dimethyl aziridine, which is applied in the field of synthesis D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide , can solve the problems such as unfavorable improvement of product purity, low industrial production yield, unfavorable forward reaction, etc., and achieve the effect of shortening the production cycle, reducing the reaction time, and reducing the operation difficulty coefficient.

Inactive Publication Date: 2020-08-18
南通森萱药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] , the original industrial production uses dichloromethane as a solvent, and reacts at ≦0°C for 24 to 36 hours. The reaction raw materials of Kanzhongkong ≦0.2% are filtered to remove amine salts, and the dichloromethane is dried under reduced pressure at 30°C, and ethyl acetate is added. The ester is crystallized to obtain a crude product. After washing with water and ethanol, 99% of the pure product is obtained. The product is dissolved in the solution at the same time, which is not conducive to the forward reaction. The industrial production yield is low and the cycle is long, and the impurities generated in the reaction are relatively high. , is not conducive to improving product purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] a. D-phenylalanine is reduced to D-phenylalaninol:

[0024] Mix 95g of D-phenylalanine, 800g of dioxane, and 69g of sodium borohydride, add 40g of zinc chloride, heat up to 70°C, wait for a large number of bubbles to be released, cool down to 30°C, and add 30% sodium hydroxide dropwise The aqueous solution was quenched, until no gas was released and the dropwise addition was completed, the temperature was raised to 70°C and stirred for 1 hour, the temperature was lowered to 20°C, and 500 g of ethyl acetate was added to stand for stratification, the organic layer was washed with 200 g of water, extracted with EA, concentrated under reduced pressure at 60°C to obtain Add ethyl acetate M:M=1:1 to dissolve the crude product, recrystallize, lower the temperature, crystallize and dry to obtain D-phenylalaninol with a content of 98%;

[0025] b. D-phenylalaninol undergoes esterification and cyclization to form (D)-2-benzyl-N,N-dimethylaziridine:

[0026] Mix 56g of D-phenylal...

Embodiment 2

[0030] a. D-phenylalanine is reduced to D-phenylalaninol:

[0031] Mix 100g of D-phenylalanine, 820g of dioxane, and 74 sodium borohydride, add 45g of zinc chloride, heat up to 70°C, wait for a large number of bubbles to be released, cool down to 30°C, and add 30% sodium hydroxide dropwise The aqueous solution was quenched, until no gas was released and the dropwise addition was completed, the temperature was raised to 70°C and stirred for 1 hour, the temperature was lowered to 25°C, and 500 g of ethyl acetate was added to stand for stratification, the organic layer was washed with 200 g of water, extracted with EA, concentrated under reduced pressure at 60°C to obtain Add ethyl acetate M:M=1:1 to dissolve the crude product, recrystallize, lower the temperature, crystallize and dry to obtain D-phenylalaninol with a content of 98%;

[0032] b. D-phenylalaninol undergoes esterification and cyclization to form (D)-2-benzyl-N,N-dimethylaziridine:

[0033] Mix 61g of D-phenylalani...

Embodiment 3

[0038] a. D-phenylalanine is reduced to D-phenylalaninol:

[0039] Mix 105g of D-phenylalanine, 850g of dioxane, and 79g of sodium borohydride, then add 50g of zinc chloride, heat up to 70°C, wait for a large number of bubbles to be released, cool down to 30°C, and add 30% sodium hydroxide dropwise The aqueous solution was quenched, until no gas was released and the dropwise addition was completed, the temperature was raised to 70°C and stirred for 1 hour, the temperature was lowered to 25°C, and 500 g of ethyl acetate was added to stand for stratification, the organic layer was washed with 200 g of water, extracted with EA, concentrated under reduced pressure at 60°C to obtain Add ethyl acetate M:M=1:1 to dissolve the crude product, recrystallize, lower the temperature, crystallize and dry to obtain D-phenylalaninol with a content of 98%;

[0040] b. D-phenylalaninol undergoes esterification and cyclization to form (D)-2-benzyl-N,N-dimethylaziridine:

[0041]Mix 66g of D-phe...

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PUM

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Abstract

The invention discloses a synthesis method of (D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide, which comprises the following steps: a. reducing D-phenylalanine to obtain D-phenylalaninol, b. performing esterification and ring-closing reactions on the D-phenylalaninol to obtain (D)-2-benzyl-N,N-dimethylaziridine; and c. carrying out a reaction on the (D)-2-benzyl-N,N-dimethylaziridine with dimethylamino sulfonyl chloride to generate the (D)-2-benzyl-N,N-dimethyl aziridine-1-sulfonamide. The product has high content and purity, enhances the yield of industrial production, shortens the half timeof industrial production, and effectively considers the problems of environmental protection, cost and yield.

Description

technical field [0001] The invention relates to a new method for synthesizing D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide. Background technique [0002] D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide its structure is: [0003] , the original industrial production uses dichloromethane as a solvent, and reacts at ≦0°C for 24 to 36 hours. The reaction raw materials of Kanzhongkong ≦0.2% are filtered to remove amine salts, and the dichloromethane is dried under reduced pressure at 30°C, and ethyl acetate is added. The ester is crystallized to obtain a crude product. After washing with water and ethanol, 99% of the pure product is obtained. The product is dissolved in the solution at the same time, which is not conducive to the forward reaction. The industrial production yield is low and the cycle is long, and the impurities generated in the reaction are relatively high. , is not conducive to improving product purity. Contents of the invention [0004] The invention re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D203/24
CPCC07D203/24
Inventor 顾维龙封乃军戚小军丁勇严箐
Owner 南通森萱药业有限公司
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