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16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound as well as synthetic method and application thereof

A technology of valeryloxy acetate pregesterone alcohol and acetoxyl group is applied in the field of 16-valeryloxy acetate pregesterone alcohol compound, and can solve the problems of unstable reaction yield, difficult control of reaction process and the like, and achieves The effect of preventing the hydrolysis reaction

Inactive Publication Date: 2014-06-18
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This research has solved the environmental problem of chromic anhydride, but in the large-scale test, it is found that there are some shortcomings such as unstable reaction yield and difficult control of the reaction process.

Method used

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  • 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound as well as synthetic method and application thereof
  • 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound as well as synthetic method and application thereof
  • 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound as well as synthetic method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 compound 1a

[0029]

[0030] Compound 2a (10 g) and WO 3 (21mg, 0.005e) was dissolved in 60mL of acetone, and when heated to 50°C, 30% hydrogen peroxide (8.1mL, 4eq) was added dropwise, reacted at 50°C for 3 hours, all the raw materials were reacted, quenched with saturated aqueous sodium sulfite solution, and reduced pressure The solvent was evaporated, diluted with 100ml of toluene, washed with water, and concentrated to obtain 10.00g of compound 1a with a yield of 92.1%.

[0031] 1 H NMR (400MHz, CDCl 3 )δ5.59-5.54(m,1H),4.73-4.65(m,1H),4.22-4.18(m,1H),4.12-4.11(m,1H),3.93(d,J=4Hz,2H), 2.10(s,3H),2.08(s,3H),2.05(s,3H),2.02(s,3H),1.03(s,3H),1.01(s,3H),0.98(d,J=4Hz, 3H);

[0032] LRMS-ESI(m / z):629.2([M+Na] + );

Embodiment 2

[0033] The synthesis of embodiment 2 compound 1a

[0034]

[0035] Compound 2a (10g) and Na 2 WO 4 .2H 2 O (24mg, 0.004eq) was dissolved in 60mL butanone, and 30% hydrogen peroxide (6.1mL, 3eq) was added dropwise when heated to 70°C, and reacted at 70°C for 3 hours. The solvent was evaporated under reduced pressure, diluted with 150ml of benzene, washed with water, and concentrated to obtain 10.14g of compound 1a with a yield of 93.4%.

Embodiment 3

[0036] The synthesis of embodiment 3 compound 1b

[0037]

[0038] Compound 2b (10g) and (NH 4 ) 2 MoO 4 (21mg, 0.006eq) was dissolved in 70mL of dichloromethane, 30% hydrogen peroxide (2.0mL, 1eq) was added dropwise at room temperature, and reacted at room temperature for 24 hours. Diluted with methane, washed with water, and concentrated to obtain 10.34 g of compound 1b with a yield of 95.2%.

[0039] 1 H NMR (400MHz, CDCl3 )δ5.59-5.54(m,1H),4.74-4.68(m,1H),4.24-4.20(m,1H),4.12-4.10(m,1H),3.93(d,J=4Hz,2H), 2.11(s,3H),2.08(s,3H),2.06(s,3H),2.02(s,3H),1.03(s,3H),1.01(s,3H),0.99(d,J=4Hz, 3H);

[0040] LRMS-ESI(m / z):629.2([M+Na] + );

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Abstract

The invention relates to a 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound as well as a synthetic method and application thereof. Pseudo steroidal sapogenins are used as raw materials, and are subjected to oxidation reaction with hydrogen peroxide under the catalysis of a metal catalyst to obtain the 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound. Moreover, a 16-dehydrogenized progesterone alcohol acetate compound which is widely used industrially can be conveniently synthesized by using the 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound. The whole synthetic method disclosed by the invention has cheap and easily-available raw materials, mild reaction conditions, short operating steps, and a high total yield. The 16-(2'-hydroxyl-4'-methyl-5'-acetoxyl) amyl acyloxy acetic acid progesterone alcohol compound disclosed by the invention fundamentally improves the availability of steroidal sapogenins, solves the problems of environment pollution of a metal chromium compound existing in the original production technique, and is more beneficial for industrial production.

Description

technical field [0001] The present invention relates to a 16-(2'-hydroxyl-4'-methyl-5'-acetoxy) valeryloxyacetate progesterone alcohol compound, a synthesis method and an application thereof. They are obtained from the oxidation of hydrogen peroxide catalyzed by metal catalysts of pseudosteroidal saponins. The 16-dehydroprogesterone acetate compound widely used in industry can be conveniently synthesized by such compounds. The whole synthesis method has cheap and easy-to-obtain raw materials, mild reaction conditions, short operation steps and high overall yield. technical background [0002] 16-Dehydroprogesterone acetate compound and its analogs are important synthetic intermediates of steroid hormone drugs, and their annual production capacity is about 2,000 tons. [0003] The 16-dehydroprogesterone alcohol acetate technology currently produced still adopts the steroidal sapogenin degradation method invented by the American chemist Marker in the 1940s (Marker: J.Am.Chem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00C07J71/00
Inventor 田伟生汪昀田海龙
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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