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Novel intermediate for synthesizing teprenone and application of novel intermediate

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

Active Publication Date: 2019-04-05
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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  • Novel intermediate for synthesizing teprenone and application of novel intermediate
  • Novel intermediate for synthesizing teprenone and application of novel intermediate
  • Novel intermediate for synthesizing teprenone and application of novel intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1. Synthesis of 2-(3-chloropropyl)-2-methyl-1,3-dioxolane (formula 2)

[0057] 16.5 g of 5-chloro-2-pentanone, 150 ml of toluene, 0.5 g of p-toluenesulfonic acid, and 16.9 g of ethylene glycol were added to a 250 ml reaction flask. After the addition, the temperature of the oil bath was raised to reflux and water was separated for 4 hours. The reaction solution was cooled to room temperature and washed with sodium bicarbonate solution and water. The obtained toluene organic layer was distilled at 60° C. under reduced pressure to obtain 19.68 g of oily 2-(3-chloropropyl)-2-methyl-1,3-dioxolane (94.6% yield).

Embodiment 2

[0058] Embodiment 2. Synthesis of 2-(3-chloropropyl)-2-methyl-1,3-dioxolane (formula 2)

[0059] 16.5 g of 5-chloro-2-pentanone, 150 ml of n-hexane, 0.5 g of p-toluenesulfonic acid, and 16.9 g of ethylene glycol were added to a 250 ml reaction flask. After the addition, the oil bath was warmed up and refluxed to separate water for 4 hours. The reaction liquid was cooled to room temperature and washed with sodium bicarbonate solution and water. The obtained n-hexane organic layer was distilled at 60°C under reduced pressure to obtain 18.15 g of oily 2-(3-chloropropyl)-2-methyl-1,3-dioxolane (87.24% yield).

Embodiment 3

[0060] Example 3. Synthesis of (9E,13E)-6-hydroxyl-6,10,14,18-4methyl nonadeca-9,13,17,-trien-2-one (formula 5)

[0061] Add 1.2 g of magnesium chips, 20 ml of tetrahydrofuran, and one iodine pellet into the reaction flask. The oil bath was heated to a temperature of 50°C, then 10.4 g of 2-(3-chloropropyl)-2-methyl-1,3-dioxolane (Formula 2) was slowly added dropwise, and the temperature was raised to reflux for 2 hours after the drop was completed. Then the reaction solution was cooled to an internal temperature of 20°C, and 13.12 g of farnesyl acetone (Formula 4) was added dropwise. After the dropwise addition, the reaction was incubated for 3 hours, then the reaction solution was poured into ice cubes and stirred, and 10 ml of hydrochloric acid was added and stirred for 1 hour. , adding 50 ml of n-hexane for extraction, static layering, washing the organic layer with sodium bicarbonate, washing with saturated brine until neutral, and then evaporating the organic layer of n-h...

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Abstract

The invention discloses a novel intermediate for synthesizing teprenone. The novel intermediate is a compound shown as a formula 5. The novel intermediate has the advantages that process routes for synthesizing the teprenone by the compound shown as the formula 5 are simple, raw materials are easily available, reaction conditions are mild, side reaction rarely can be carried out, and accordingly the novel intermediate is favorable for industrial production; the high-purity teprenone can be obtained by the aid of the process routes without rectification, and the requirements on ratios of isomermono-cis-form (5Z, 9E and 13E) to all-trans-forms (5E, 9E and 13E) of the teprenone can be met.

Description

technical field [0001] The invention relates to the fields of medicine and fine chemical industry; in particular, the invention relates to a new intermediate used in the synthesis of teprenone and a new method for synthesizing teprenone using the intermediate. Background technique [0002] The chemical name of teprenone is 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraen-2-one. Teprenone is a mixture of monocis (5Z, 9E, 13E) and all trans (5E, 9E, 13E) geometric isomers (0.66:1), colorless to light yellow, with a special fragrance oily liquid. [0003] Teprenone has strong anti-ulcer effect and improvement effect on gastric mucosal lesions for various experimental ulcers and gastric mucosal lesions. Synthesis and secretion, can promote the healing of gastric mucosal damage, can improve the biosynthesis ability of prostaglandins in gastric mucosa, improve gastric mucosal blood flow, suitable for the treatment of acute gastritis, gastric ulcer, etc. Teprenone was launched i...

Claims

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Application Information

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Patent Type & Authority Applications(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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