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A kind of intermediate synthesized by teprenone and its application

A teprenone and reaction technology, applied in the field of synthesizing teprenone and new intermediates for teprenone synthesis, can solve the problems of low total yield, long synthesis steps and high synthesis cost

Active Publication Date: 2021-12-28
HUANGGANG LUBAN PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis steps of these two methods are relatively long, the total yield is low, and the synthesis cost is higher

Method used

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  • A kind of intermediate synthesized by teprenone and its application
  • A kind of intermediate synthesized by teprenone and its application
  • A kind of intermediate synthesized by teprenone and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1. Synthesis 2- (3-chloropropyl) -2-methyl-1,3-dioxolane (formula 2)

[0061] 5-chloro-2-pentanone 16.5 g, toluene was added to 150 ml of toluene sulfonic acid, 0.5 g of toluenesulfonic acid, 16.9 g of ethylene glycol. After the addition, the oil bath was returned and refluxed for 4 hours. The reaction liquid cooling room temperature was washed with sodium bicarbonate solution and washed. The obtained toluene organometh was 60 ° C, distilled to the oil 2- (3-chloropropyl) -2-methyl-1,3-dioxopenyl ring 19.68 g (yield 94.6%).

Embodiment 2

[0062] Example 2. Synthesis 2- (3-chloropropyl) -2-methyl-1,3-dioxolane (formula 2)

[0063] 5-chloro-2-pentanone 16.5 g of 5-chloro-2-pentanone was added to 250 ml of reaction flask, 0.5 g of toluenesulfonic acid, 16.9 g of ethylene glycol. After the addition, the oil bath was stirred back water for 4 hours. The reaction liquid cooling room temperature was washed with sodium bicarbonate solution and washed. The obtained n-hexane organic layer was 60 ° C, distilled to the oil 2- (3-chloropropyl) -2-methyl-1,3-dioxoprophip 18.15 g (yield 87.24%).

Embodiment 3

[0064] Example 3. Synthesis (9E, 13E) -6-hydroxy-6, 10, 14, 18-4 methyl nine-9, 13, 17, - tri-2-ketone (formula 5)

[0065] Magnesium films were added to 1.2 g, tetrahydrofuran 20 ml, one iodine particles. The oil bath was heated to a temperature 50 ° C, then 2- (3-chloropropyl) -2-methyl-1,3-dioxoprophip (Equina 2) was slowly added dropwise, and the temperature was refluxed for 2 hours. The reaction solution was then lowered to 20 ° C for 10 ° C, and the Nikyl acetone (formula 4) was added dropwise, and the incubation was added dropwise to the insulation reaction for 3 hours, and then the reaction solution was poured into the ice cubes, stirring 10 ml of hydrochloric acid for 1 hour Add 50 ml of n-hexane extraction, stationary layers, sodium hydrogencarbonate, saturated brine, then washed to neutral, and then n-hexane organic layers below 60 ° C, evaporated to evaporation of the solvent (9E, 13E) -6-hydroxy-6,10,14,18-4 methyl nine-9, 13, 17, tri-2-ketone (formula 5) 9.4 g (yield...

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PUM

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Abstract

The invention discloses a new intermediate for synthesizing teprenone, the compound of formula 5. The process route for synthesizing teprenone by using the compound of formula 5 is simple, the raw materials are readily available, the reaction conditions are mild, and the side reactions are few, thereby facilitating industrial production. The process route of the invention can obtain tepril with high purity and the ratio of isomer monocis (5Z, 9E, 13E) and all trans (5E, 9E, 13E) meets the requirements without rectification ketone.

Description

Technical field [0001] The present invention relates to medicine and chemical art; in particular, the present invention relates to novel intermediates for synthesis of teprenone and intermediates for the synthesis of a new method of use of teprenone. Background technique [0002] Alternatively chemical GGA (teprenone) called 6,10,14,18- tetrakis nineteen -5,9,13,17- tetramethyl-2-one. Teprenone as a single cis (5Z, 9E, 13E), and (5E, 9E, 13E) all-trans-geometric isomers: a mixture of (1 0.66) as a colorless to pale yellow, special flavor oily liquid. [0003] Teprenone has a strong anti-ulcer effect and gastric lesions improving action of various experimental ulcers and gastric mucosal lesions, promotes the gastric mucosa, gastric mucus reproducing the main defensive factor, molecular glycoproteins, phospholipids synthesis and secretion, can promote healing of gastric mucosal damage, can improve the ability of the gastric mucosa in the biosynthesis of prostaglandins, improve gast...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/24C07C45/64C07C49/203C07C45/66C07F3/02
CPCC07C45/64C07C45/66C07C49/203C07C49/24C07F3/02
Inventor 杨小龙裴啤兵张建军陈潜杨铁波
Owner HUANGGANG LUBAN PHARM
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