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Synthesis method of 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid

A technology of tert-butoxycarbonyl, synthesis method, applied in 8-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5-hydrogen-imidazole[1,5-a][1,4 ] The field of synthesis of diaza-6-carboxylic acid, achieving the effects of stable and easy-to-control reaction conditions, reasonable design, and convenient purification

Active Publication Date: 2016-06-22
SHANGHAI SYNTHEALL PHARM CO LTD +2
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

The main solution is that there is no suitable industrial synthesis of 8-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5-hydro-imidazol[1,5-a][1,4]diazepine-6 -Technical issues with the method for carboxylic acids

Method used

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  • Synthesis method of 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid
  • Synthesis method of 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid
  • Synthesis method of 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] Add 30 g of compound 2 into the methanol solution, add thionyl chloride dropwise at low temperature, and react at room temperature for 12 h. The solvent was spin-dried, and the crude product was dissolved in dichloromethane, washed with ammonium chloride aqueous solution, and purified on a silica gel column. The yield: 70%.

[0016] HNMR (MeOD): δ 7.77 (d, 2H), 3.85 (s, 3H).

Embodiment 2

[0018]

[0019] 300 g of compound 2 was added to the methanolic hydrochloric acid solution and refluxed for 20 hours. TLC (dichloromethane: methanol volume ratio = 10: 1, R f =0.4) shows the end of the reaction. The solvent was spin-dried, and the methanol solution of the crude triethylamine was neutralized to pH=9, and the solvent was spin-dried again, and the crude product was dissolved in dichloromethane, and used directly in the next reaction without purification. The yield is about 100%.

[0020] HNMR (MeOD): δ 7.77 (d, 2H), 3.85 (s, 3H).

[0021] Synthesis of (2-(ethoxycarbonyl)allyl)-5-methyl carboxylate-imidazole

[0022]

[0023] 600 g of compound 3 and triethylamine were added into dichloromethane, and 2-bromomethyl-ethyl acrylate was slowly added dropwise to the reaction system at 0°C. After the dropwise addition, TLC (dichloromethane: methanol volume ratio=20:1, R f =0.5) shows that the reaction is over, and the crude product is directly purified by a ...

Embodiment 3

[0035]

[0036] 100 grams of compound 5 and 40 grams of palladium carbon were dissolved in an ethanol solution, and the system was reacted at 50° C. and a hydrogen pressure of 50 Pa for 6 hours. TLC (petroleum ether: ethyl acetate volume ratio = 2: 1, R f =0.6) shows the end of the reaction. The solution was filtered with celite, and the filtrate was spin-dried to obtain a crude product, which was washed with ethyl acetate, filtered, and dried to obtain Compound 6, yield: 82%. HNMR (CDCl3): δ7.90(s,1H),7.65(s,1H),4.21(m,2H),4.05-3.96(m,2H),3.44-3.25(m,2H),315-3.00( m, 1H), 1.29(3H).

[0037] tert-butyl-6-methyl-9-oxo-6,7-dihydro-5-hydro-imidazol[1,5-a][1,4]diaza-6,8(9-hydrogen)-di Synthesis of Carboxylate

[0038]

[0039] 29 g of compound 6 and 8.5 g of dimethylaminopyridine were dissolved in dichloromethane solution, di-tert-butyl carbonate was slowly added at room temperature, and the reaction was stirred overnight at room temperature after the addition was comp...

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Abstract

The invention relates to a synthesis method of 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid. In the method, 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid is synthesized from easily-available 1-hydroimidazole-4, 5-dicarboxylic acid as the raw material by ten steps. And 8-(tert-butyloxycarbonyl)-6, 7, 8, 9-tetrahydro-5-hydro-imidazole[1, 5-a][1, 4]diaza-6-carboxylic acid is a useful organic synthesis intermediate.

Description

technical field [0001] The present invention relates to the practical application of 8-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5-hydro-imidazol[1,5-a][1,4]diazepine-6-carboxylic acid synthetic method. Background technique [0002] 8-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5-hydro-imidazol[1,5-a][1,4]diazepine-6-carboxylic acid (CAS No.: 1251003 -93-6) is a useful intermediate in organic synthesis. There are few reports on the industrial synthesis of this intermediate. All kinds of derivatives with this compound as the core have important roles in organic synthesis and drug synthesis. Contents of the invention [0003] The purpose of this invention is to develop a new 8-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5-hydro-imidazol[1,5-a][1,4]diazepine - Synthetic method of 6-carboxylic acid. The main solution is that there is no suitable industrial synthesis of 8-(tert-butoxycarbonyl)-6,7,8,9-tetrahydro-5-hydro-imidazol[1,5-a][1,4]diazepine-6 -Technical problems with th...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D233/90
Inventor 刘月领徐学芹周强刘璇何燕平安自强于华夏章洋张同心白雪毛延军于凌波何振民马汝建陈民章傅小勇王文贵
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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