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Amide Boc de-protection method

A kind of amide, selected technology, applied in the field of organic synthesis, can solve the problems of not being widely used, unfriendly to the environment, toxicity and corrosion

Inactive Publication Date: 2018-08-24
CHANGSHU INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have defects, such as certain toxicity and corrosiveness, unfriendly to the environment, and general yield, so they cannot be widely used.

Method used

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  • Amide Boc de-protection method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1, 3-methyl-N-phenylbenzamide

[0089]

[0090]

[0091] Weigh 0.5mmol amide III-1, 1% molar amount of palladium catalyst, 1mmol potassium carbonate in the Schlenk reaction tube, feed nitrogen into the double row tube, repeat three times, then open the large nitrogen valve, inject 0.75mmol aniline, add 2ml new Evaporate tetrahydrofuran and close the valve. The test tube was stirred at room temperature for 10 minutes and then placed at 110°C for 24 hours. After the reaction, spot the plate with TLC, spin dry tetrahydrofuran, add water, extract repeatedly three times with ethyl acetate, then dry with anhydrous magnesium sulfate, spin dry, and get 0.495 mmol (104.5 mg) of white crystals by column chromatography, which is the product 3-Methyl-N-phenylbenzamide, yield 99%.

[0092] 1 H NMR (400MHz, CDCl 3 )δ7.90(s, 1H), 7.71-7.58(m, 4H), 7.35(dd, J=8.8, 6.7Hz, 4H), 7.14(t, J=7.4Hz, 1H), 2.41(s, 3H ). 13 C NMR (101MHz, CDCl 3 )δ166.01, 138.71, 138.02, ...

Embodiment 2

[0093] Embodiment 2, 3-methyl-N-naphthalene-1-yl-benzamide

[0094]

[0095] Weigh 0.5mmol amide III-1, 1% molar palladium catalyst, 1mmol potassium carbonate, 0.75mmol 1-naphthylamine in the Schlenk reaction tube, feed nitrogen into the double-row tube, repeat three times, then open the large nitrogen valve, add fresh steam 2ml tetrahydrofuran, close the valve. The test tube was stirred at room temperature for 10 minutes and then placed at 110°C for 24 hours. After the reaction was completed, TLC spotting, spin-dried tetrahydrofuran, added water, repeated extraction three times with ethyl acetate, then dried with anhydrous magnesium sulfate, spin-dried, and column chromatography obtained 0.425 mmol (111.8 mg) of white crystals of the product, namely Product 3-methyl-N-naphthalen-1-yl-benzamide, yield 85%.

[0096] 1H NMR (400MHz, CDCl3) δ8.20(s, 1H), 8.03(d, J=7.1Hz, 1H), 7.93-7.87(m, 2H), 7.81(s, 1H), 7.75(t, J= 7.6Hz, 2H), 7.57-7.48(m, 3H), 7.45-7.36(m, 2H), 2.46(s, 3...

Embodiment 3

[0097] Embodiment 3, 3-phenyl-N-(2-methylphenyl) benzamide

[0098]

[0099] Weigh 0.5mmol amide III-1, 1% molar amount of palladium catalyst, 1mmol potassium carbonate, 0.75mmol 2-methylaniline in the Schlenk reaction tube, feed nitrogen into the double row pipe, repeat three times, then open the nitrogen valve, add Freshly steam 2ml of tetrahydrofuran and close the valve. The test tube was stirred at room temperature for 10 minutes and then placed at 110°C for 24 hours. After the reaction, TLC plate, spin dry THF, add water, repeat extraction three times with ethyl acetate, then dry with anhydrous magnesium sulfate, spin dry, column chromatography to obtain the product white crystal 0.48mmol (108.0mg), namely Product 3-phenyl-N-(2-methylphenyl)benzamide, yield 96%.

[0100] 1 H NMR (400MHz, CDCl 3 )δ7.93(d, J=7.9Hz, 1H), 7.71(s, 1H), 7.65(d, J=4.1Hz, 2H), 7.42-7.33(m, 2H), 7.24(t, J=11.4 Hz, 2H), 7.12(d, J=7.4Hz, 1H), 2.44(s, 3H), 2.33(s, 3H). 13 C NMR (101MHz, CDCl...

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Abstract

The invention discloses an amide Boc de-protection method. The amide Boc de-protection method includes carrying out reaction on Boc protected amide III and amine IV under the condition of the presenceof palladium catalysts to generate new amide V. 8-aminoquinoline can be used as a guide group to be applied to chemical reaction, a process for synthesizing the new amide by means of de-protection isprovided, protecting groups can be easily removed by means of palladium catalysis, the new amide can be generated, and the reaction is high in efficiency. The amide Boc de-protection method has the advantages of environmental friendliness, recyclability and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for removing Boc protection of amides. Background technique [0002] As a common directing group, 8-aminoquinoline is often embedded in compounds, but how to remove 8-aminoquinoline after the reaction is a problem worth thinking about. Existing method mainly contains two kinds, and the first kind can be decomposed into amide under ice bath with cerium ammonium nitrate (CAN); The second kind is used to generate carboxylic acid under the effect of lithium hydroxide and hydrogen peroxide. However, these methods have defects, such as certain toxicity and corrosiveness, unfriendly to the environment, and average yields, so they cannot be widely used. Contents of the invention [0003] Purpose of the invention: In order to solve the above-mentioned problems in the prior art, the present invention provides a method for de-Boc protection of amides, the method is r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07C233/65C07C233/75C07C233/66C07C233/29C07C235/56C07D317/58
CPCC07C231/10C07C2601/14C07D317/58C07C233/65C07C233/75C07C233/66C07C233/29C07C235/56Y02P20/55
Inventor 袁荣鑫吴问刚易钧唐晓艳程洪见殷文宇付任重马运声
Owner CHANGSHU INSTITUTE OF TECHNOLOGY
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