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Preparation method of catalyst intermediate

A compound and time-fixed technology, applied in the field of preparation of catalyst intermediates, can solve the problems of unsuitable for pilot scale-up, weak selectivity, poor selectivity, etc., and achieve the effects of low cost, simple process, control and stability of ee value

Pending Publication Date: 2021-01-19
DONGGUAN HEC GENERIC DRUG R&D CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For N-[(1R, 2R)-2-amino-1,2-diphenylethyl]-1,1,1-trifluoromethanesulfonic acid amide is synthesized with few related documents, in the prior art (CN 102304007) is prepared by the reaction of (1R,2R)-1,2-diphenylethylenediamine and trifluoromethanesulfonyl chloride. The preparation method has poor selectivity, and post-treatment requires column chromatography to obtain a relatively pure product. Not only limited to post-treatment, but also has disadvantages such as low selectivity, low yield, and more impurities, and this method is not suitable for pilot scale-up

Method used

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  • Preparation method of catalyst intermediate
  • Preparation method of catalyst intermediate
  • Preparation method of catalyst intermediate

Examples

Experimental program
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Embodiment 1

[0031] The preparation of embodiment 1 compound (II)

[0032] Add 600ml of dichloromethane and 100g of compound (I) into a 2L four-neck flask, stir and cool down to -10°C, add 22.6g of methanesulfonic acid dropwise at one time, stir for 0.5 hours, control the temperature below 0°C and slowly add Tf 2 O in dichloromethane (Tf 2 O: 132.90g, dichloromethane: 300ml), the dropwise addition is completed, and the control is sampled after 1 hour of heat preservation reaction;

[0033] After the reaction is complete, add 200ml of drinking water, adjust the pH to 7-8 with 10% aqueous sodium hydroxide solution, raise the temperature to 15°C, let stand to separate layers, wash the organic layer once with 200ml of drinking water, and evaporate the organic layer to dryness under reduced pressure to obtain the crude product ;

[0034] Add 900ml of methyl tert-butyl ether to the crude product, heat up to 55°C, keep stirring for 0.5 hours, cool down to 25°C, filter, and dry in vacuo to obtai...

Embodiment 2

[0035] The preparation of embodiment 2 compound (II)

[0036] Add 600ml of dichloromethane and 100g of compound (I) into a 2L four-neck flask, stir and cool down to -10°C, add 45.27g of methanesulfonic acid dropwise at one time, stir for 0.5 hours, control the temperature below 0°C and slowly add Tf 2 O in dichloromethane (Tf 2 O: 132.90g, dichloromethane: 300ml), the dropwise addition is completed, and the control is sampled after 1 hour of heat preservation reaction;

[0037] After the reaction is complete, add 200ml of drinking water, adjust the pH to 7-8 with 10% aqueous sodium hydroxide solution, raise the temperature to 15°C, let stand to separate layers, wash the organic layer once with 200ml of drinking water, and evaporate the organic layer to dryness under reduced pressure to obtain the crude product ;

[0038]Add 900ml of methyl tert-butyl ether to the crude product, raise the temperature to 55°C, keep stirring for 0.5 hours, cool down to 25°C, filter, and dry in ...

Embodiment 3

[0039] The preparation of embodiment 3 compound (II)

[0040] Add 600ml of dichloromethane and 100g of compound (I) into a 2L four-neck flask, stir and cool down to -10°C, add 31.81g of trifluoromethanesulfonic acid dropwise at one time, stir for 0.5 hours, and slowly add dropwise while controlling the temperature not exceeding 0°C Tf 2 O in dichloromethane (Tf 2 O: 132.90g, dichloromethane: 300ml), the dropwise addition is completed, and the control is sampled after 1 hour of heat preservation reaction;

[0041] After the reaction is complete, add 200ml of drinking water, adjust the pH to 7-8 with 10% aqueous sodium hydroxide solution, raise the temperature to 15°C, let stand to separate layers, wash the organic layer once with 200ml of drinking water, and evaporate the organic layer to dryness under reduced pressure to obtain the crude product ;

[0042] Add 900ml of methyl tert-butyl ether to the crude product, heat up to 55°C, keep stirring for 0.5 hours, cool down to 2...

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Abstract

The invention relates to a preparation method of a catalyst intermediate, and in particular, relates to a preparation method of N-[(1R,2R)-2-amino-1,2-diphenyl ethyl]-1,1,1-trifluoromethanesulfonic acid amide, and belongs to the field of medicinal chemistry. The preparation method comprises the steps: salifying (1R,2R)-1,2-diphenylethylenediamine with an acid to reduce the activity of one amino group, and directly reacting the other amino group with trifluoromethanesulfonic anhydride to synthesize N-[(1R,2R)-2-amino-1,2-diphenylethyl]-1,1,1-trifluoromethanesulfonic acid amide in one step. Thepreparation method disclosed by the invention is simple in process, high in yield, low in cost, good in selectivity and friendly in reaction condition, and the ee value of the product can be well controlled and stabilized; the method has important industrial application value.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, and relates to a preparation method of a catalyst intermediate, in particular to a catalyst intermediate N-[(1R,2R)-2-amino-1,2-diphenylethyl]-1,1, Preparation method of 1-trifluoromethanesulfonic acid amide. Background technique [0002] The asymmetric and efficient synthesis of chiral compounds with high enantioselectivity has attracted increasing attention in the fields of chemical industry, agriculture, animal husbandry and medicine, especially in the pharmaceutical industry. The mainstream (A.M.Rouhi, "Chiralchemistry", Chem.Eng.News 2004, 82, 47), asymmetric catalytic hydrogenation is one of the main methods for the efficient preparation of chiral compounds. [0003] Asymmetric catalytic reactions use chiral catalysts to control the stereoselectivity of products, and use achiral products to convert chiral products to achieve chiral proliferation and chiral amplification. N-[(1R,2R)-2-am...

Claims

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Application Information

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IPC IPC(8): C07C303/38C07C311/05
CPCC07C303/38C07C311/05
Inventor 陈明洪黎利军王仲清范文进邹敬源漆春辉李利锋罗忠华黄芳芳
Owner DONGGUAN HEC GENERIC DRUG R&D CO LTD
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