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Novel preparation method and intermediate of prostaglandin

A technology for prostaglandins and compounds, applied in the field of chemical synthesis, can solve the problems affecting the application of prostaglandins, the complex preparation process of intermediate VIII, etc.

Active Publication Date: 2021-04-30
CHANGZHOU BOHIV PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Therefore, the preparation process of the intermediate VIII synthesized by this synthetic method is complicated, which affects its application in the synthesis of prostaglandins

Method used

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  • Novel preparation method and intermediate of prostaglandin
  • Novel preparation method and intermediate of prostaglandin
  • Novel preparation method and intermediate of prostaglandin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] The preparation of the compound shown in embodiment 1. structural formula (III)

[0115]

[0116] The preparation method of 2-methylcyclopentadiene shown in structural formula (II) can be referred to Tetrahedron.,1965,21,2313-2327, and it can obtain monomer by pyrolysis of the methylcyclopentadiene dimer of commercialization supply , so that the current production and current use

[0117]

[0118] Dissolve the compound represented by structural formula (II) (80.1g, 1.0mol) in MeOH (400.0ml), add rose bengal (8.0g), cool down to -30°C, feed oxygen, and keep warm at -30°C under light for reaction 2 hours, then overnight at room temperature. Add thiourea (76.0 g, 1.0 mol) and react at room temperature for 6 h. Post-processing: the reaction solution was washed into ice water, extracted 3 times with dichloromethane, the dichloromethane layers were combined, washed with water and saturated brine, layered, the organic layer was dried over anhydrous magnesium sulfate, f...

Embodiment 2

[0121] The preparation of the compound shown in embodiment 2. structural formula (IV)

[0122]

[0123] Dissolve the compound (57.0g, 0.5mol) shown in structural formula (III) in THF (350.0ml), stir to dissolve, add vinyl acetate (100.0ml), then add lipase AK (2.8g, Amano Enzyme Co., Ltd. ). After the addition, react at room temperature for 7 hours. Post-processing: filter the reaction solution, concentrate the filtrate, dissolve the residual oily substance with ethyl acetate, wash with water and saturated brine, separate layers, dry the organic layer with anhydrous magnesium sulfate, filter, and concentrate the filtrate to dryness to obtain the product: 71.8g (Yield 92.0%).

[0124] [a] 25 D =-68.6° (C=1.0, CHCl 3 )

[0125] 1 H-NMR (CDCl 3 )δ1.660(dt,1H),δ1.713(s,3H),δ2.063(s,3H),δ2.850(dt,1H),δ4.700-4.750(m,1H),δ5. 470-5.530(m,1H), δ5.970-6.010(m,1H).

[0126] MS (ES + ) 156.1.

Embodiment 3

[0127] The preparation of the compound shown in embodiment 3. structural formula (V) (R 1 = tert-butyldimethylsilyl)

[0128]

[0129] Dissolve the compound (46.8g, 0.3mol) shown in structural formula (IV) in DMF (468.0ml), stir to dissolve, add imidazole (61.0g, 0.9mol), add tert-butyldimethylsilyl chloride (67.8 g, 0.45mol), the addition was completed, and the reaction was carried out at room temperature for 3 hours. Post-processing: wash the reaction solution into ice water, extract 3 times with ethyl acetate, combine the ethyl acetate layers, wash with water in turn, wash with saturated brine, separate layers, dry the organic layer with anhydrous magnesium sulfate, filter, and concentrate the filtrate to Dry to obtain oil: 79.5 g (98.0% yield).

[0130] 1 H-NMR (CDCl 3 )δ0.170(s,6H),δ0.971(s,9H),δ1.640(dt,1H),δ1.721(s,3H),δ2.120(s,3H),δ2.870( dt, 1H), δ4.550-4.610 (m, 1H), δ5.560-5.620 (m, 1H), δ6.010-6.140 (m, 1H).

[0131] MS (ES + )270.65.

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Abstract

The invention provides an optically active cyclopentanone compound shown as a formula (I) and a preparation method thereof. The optically active cyclopentanone compound can be used for preparing key intermediates and derivatives thereof in prostaglandin synthesis. The invention also provides a method for synthesizing prostaglandin by using the optically active cyclopentanone compound. When the optically active cyclopentanone compound is used for synthesizing prostaglandin, the synthesis steps of prostaglandin can be remarkably shortened, the synthesis efficiency is improved, and the production cost is reduced.

Description

technical field [0001] The present invention relates to the field of chemical synthesis. Specifically, the present invention relates to a novel intermediate process for the preparation of prostaglandins, a process for the preparation of the intermediate, and a novel process for the preparation of prostaglandins using the intermediate. Background technique [0002] Prostaglandins (PGs) are a class of important endogenous natural products with multiple biological activities. They play an important role in the reproductive system, respiratory system, digestive system and cardiovascular system. It can cause the body's defense reactions such as inflammation and pain, and can regulate physiological and pathological processes such as pregnancy, hypertension, ulcers, asthma, glaucoma and pain, and is an important mediator of various physiological processes. [0003] The structure of prostaglandins has more chirality, and the synthesis is difficult. Early famous chemists made a lot...

Claims

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Application Information

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IPC IPC(8): C07C405/00C07D303/32C07D407/04C07F7/18
CPCC07C405/00C07D303/32C07F7/1804C07F7/1892C07D407/04C07C2601/10Y02P20/55
Inventor 刘向群陈宣福李强
Owner CHANGZHOU BOHIV PHARM TECH CO LTD
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