The method of synthesizing (s)-2-benzyloxypropanal

A technology of benzyloxypropionaldehyde and benzyloxypropionic acid is applied in the directions of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc. High production cost, high price and other problems, to achieve the effect of improving operation safety, easy operation and reducing production cost

Active Publication Date: 2021-06-11
东营睿港投资服务有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This method will use the diisobutyl aluminum hydride that is expensive and easy to catch fire during post-processing, resulting in the production of S-2-benzyloxy propionaldehyde is dangerous and the production cost is high

Method used

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  • The method of synthesizing (s)-2-benzyloxypropanal
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  • The method of synthesizing (s)-2-benzyloxypropanal

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Effect test

Embodiment 1

[0026] 1. Add (S)-2-benzyloxypropionic acid (18.02 grams, 0.10mol), ethylenediamine (7.21 grams, 0.12mol) and 150ml toluene to a 250ml round bottom flask equipped with a water separator, and heat to reflux And divide the water. When the separated water reached 1.60ml (0.09mol), the heating was stopped, and the toluene was removed by rotary evaporation, and the resulting reaction mixture was heated to 150°C for two hours under a pressure of 10 mm Hg to obtain (S)-2-(1-benzyl 17.77 g (0.087 mol) of oxyethyl)-4,5-dihydro-1H-imidazole, yield 87%. The NMR data of (S)-2-(1-benzyloxyethyl)-4,5-dihydro-1H-imidazole is: 1H NMR (400MHz, CDCl ): δ=1.19(d, 3H), 2.77( t, 2H), 3.41(t, 2H), 3.92(q, 1H), 4.49(s, 2H), 6.97(s, 1H), 7.27~7.35(br, 5H); HRMS(ESI) calcd for C12H16N2O[ M+H]+205.1336, found 205.1358; fully proved to be consistent with the structure of (S)-2-(1-benzyloxyethyl)-4,5-dihydro-1H-imidazole obtained in the present invention.

[0027] 2. Dissolve 20.43 g (0.10 mol) of (S)...

Embodiment 2

[0029] 1. Add (S)-2-benzyloxypropionic acid (0.10mol), ethylenediamine (0.13mol) and 160ml toluene into a 250ml round bottom flask equipped with a water separator, heat to reflux and separate water. When the separated water reached 1.70ml, the heating was stopped, and the toluene was removed by rotary evaporation, and the resulting reaction mixture was heated to 150°C for two hours under a pressure of 10 mm Hg to obtain (S)-2-(1-benzyloxyethyl )-4,5-dihydro-1H-imidazole 17.36 g, yield 85%; (S)-2-(1-benzyloxyethyl)-4,5-dihydro-1H-imidazole NMR data is : 1H NMR (400MHz, CDCl3): δ=1.19(d, 3H), 2.77(t, 2H), 3.41(t, 2H), 3.92(q, 1H), 4.49(s, 2H), 6.97(s, 1H), 7.27~7.35 (br, 5H); HRMS (ESI) calcd forC12H16N2O[M+H]+205.1336, found 205.1358; fully confirmed (S)-2-(1-benzyloxyethyl base)-4,5-dihydro-1H-imidazole structure is consistent.

[0030] 2. Dissolve 0.10mol of (S)-2-(1-benzyloxyethyl)-4,5-dihydro-1H-imidazole in 100ml of absolute ethanol, add metal sodium wire, 0.30mol under ...

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Abstract

The invention discloses a method for synthesizing (S)-2-benzyloxypropanal, the steps comprising: first reacting (S)-2-benzyloxypropionic acid with ethylenediamine to obtain (S)-2-( 1‑benzyloxyethyl)‑4,5‑dihydro‑1H‑imidazole; (S)‑2‑(1‑benzyloxyethyl)‑4,5‑dihydro‑1H‑imidazole was dissolved in Water and ethanol, and then add sodium metal under the protection of nitrogen to stir the reaction; after the reaction, remove the ethanol, and slowly add the residue to the saturated oxalic acid solution under the protection of nitrogen, stir evenly and then reflux for reaction. After the reaction is completed, extract, dry, filter, and remove The product (S)‑2‑benzyloxy propanal is obtained after solvent. The present invention prepares (S)-2-benzyloxypropanal in two steps; the preparation process does not use diisobutylaluminum hydride which is expensive and easy to catch fire during post-treatment, thereby fully improving the operational safety and reducing the Production cost; the preparation process is mild and easy to operate, without the anhydrous conditions required by traditional process reactions, and it is easy to realize industrial production.

Description

technical field [0001] The invention relates to the technical field of synthesis of posaconazole intermediates, specifically designing a method for synthesizing (S)-2-benzyloxypropanal. Background technique [0002] Posaconazole (chemical name: 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-tri Azol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypentan-3 -base]-1,2,4-triazole-3-ketone, English name: Posaconazole), the structural formula is as follows: [0003] [0004] Developed by the Schering-Plough Company of the United States and approved by the FDA in September 2006, it is a broad-spectrum triazole antifungal drug with high lipophilicity. The trade name is Noxafil (Nuo Kefei), oral suspension, mainly used to prevent invasive aspergillus and candida infections in patients aged thirteen and over, and to treat oropharyngeal candida infections and resistance to fluconazole and voriconazole Medicine for oropharyngeal candidiasis....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/56C07C47/277
CPCC07B2200/07C07C45/562C07D233/22C07C47/277
Inventor 田伟郑培灿王春春
Owner 东营睿港投资服务有限责任公司
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