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Preparation method of all-trans-teprenone

A teprenone, all-trans technology, applied in the field of chemical synthesis of all-trans teprenone, can solve the problems of low yield and the like

Pending Publication Date: 2022-02-11
安徽先和医药研究有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Patent CN102627539B reports the synthesis method of all-trans teprenone, through carroll rearrangement of geranyl linalool and ethyl acetoacetate to obtain mixed teprenone, and then purified by ultra-low temperature crystallization to obtain all-trans teprenone , this method first obtains mixed teprenone and then purifies, the cis-body contains 40%, the total yield after purification is about 35%, and the yield is low

Method used

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  • Preparation method of all-trans-teprenone
  • Preparation method of all-trans-teprenone
  • Preparation method of all-trans-teprenone

Examples

Experimental program
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Embodiment 1

[0023] Synthetic geranylgeranyl bromide

[0024] Add geranylgeraniol (200g, 0.688mol, Beijing Bailingwei Technology Co., Ltd.), pyridine (48g, 0.607mol) and methyl tert-butyl ether (1000ml) into the flask, cool to -5°C under nitrogen protection, drop Add phosphorus tribromide (260g, 0.961mol), after the dropwise addition, heat up to room temperature for reaction, keep warm for 2h, filter with suction, wash the organic phase once with 5% sodium carbonate, wash once with water, dry over anhydrous sodium sulfate, and filter with suction. The mother liquor was evaporated to dryness at 20°C to obtain 230 g of geranylgeranyl bromide liquid with a yield of 94.6%. 1 HNMR (CDC13), δ: 1.56(S,9H); 1.66(S,6H); 1.9-2.08(m,12H); 4.09(d,2H); 5.07(t,3H); 5.40(t,1H) ).

Embodiment 2

[0026] Synthesis of teprenone

[0027] Add geranylgeranyl bromide 100g (283mmol) into the flask, then add acetone 500ml, cuprous iodide 53.9g (283mmol), stir to dissolve, cool to -10°C, add dropwise LDA36.4g (339.6mmol), control Temperature below 0°C, rise to room temperature after dripping, keep warm for 12 hours, post-treatment, distill off excess acetone, add 500ml of n-hexane to dissolve, wash twice with saturated ammonium chloride aqueous solution, then wash once with saturated sodium chloride, Dry over anhydrous sodium sulfate, filter with suction, and evaporate the mother liquor to dryness at 40°C to obtain 90.1 g of the crude product, with a yield of 96.3%. The gas chromatogram is as follows: image 3 , with the commercially available preparation teprenone (Eisai (China) Pharmaceutical Co., Ltd.) as a contrast, the gas chromatogram is as follows Figure 4 (The cis-trans ratio is cis:trans=2:3), the gas phase spectrum of the all-trans teprenone crude product and the co...

Embodiment 3

[0029] Synthesis of teprenone

[0030] Add geranylgeranyl bromide 100g (283mmol) into the flask, then add acetone 500ml, cuprous iodide 53.9g (283mmol), stir to dissolve, cool to -10°C, add dropwise LDA42.5g (396.2mmol), control Temperature below 0°C, rise to room temperature after dripping, keep warm for 12 hours, post-treatment, distill off excess acetone, add 500ml of n-hexane to dissolve, wash twice with saturated ammonium chloride aqueous solution, then wash once with saturated sodium chloride, Dry over anhydrous sodium sulfate, filter with suction, and evaporate the mother liquor to dryness at 40°C to obtain 88 g of crude product, with a yield of 94.1%. The crude product was rectified with a thorn rectifier to obtain 75.6g of teprenone finished product, with a yield of 80.8%, and a purity of 100% as detected by HPLC.

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Abstract

The invention provides a synthetic method of all-trans-teprenone. According to the method, specific raw materials are selected and combined with a proper catalyst, firstly geranyl geranyl bromide is prepared, and then the geranyl geranyl bromide reacts with acetone and lithium diisopropylamide in the presence of cuprous iodide to synthesize all-trans-teprenone. The method is high in process yield and high in purity, and a new thought is provided for synthesis of all-trans-teprenone.

Description

technical field [0001] The invention relates to the preparation of teprenone, in particular to a method for chemically synthesizing all-trans teprenone. Background technique [0002] All-trans teprenone is 6,10,14,18-tetramethyl-5E,9E,13E,17-nonadecatetraen-2-one, a colorless to pale yellow oily liquid. [0003] Currently, teprenone on the domestic market is a cis-trans mixture, of which only all-trans teprenone plays a therapeutic role. As a new gastric mucosal protective agent for the treatment of gastric ulcer, it has unique physical and chemical properties and a good anti-ulcer mechanism. It can increase the secretion of gastric mucus, maintain the integrity of gastric mucosal barrier structure and function, promote the synthesis of endogenous prostaglandins in gastric mucosa, and effectively increase gastric mucosal blood flow, so it can significantly improve the healing rate of gastric ulcer, and is effective for chronic gastritis Both gastric mucosal damage caused by...

Claims

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Application Information

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IPC IPC(8): C07C49/203C07C45/68
CPCC07C45/68C07C17/16C07C49/203C07C21/215
Inventor 邓勤军张晓倩黄树青袁毅
Owner 安徽先和医药研究有限公司
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