Method for producing steroid compound

A compound and cholesteric technology, applied in the field of preparation of steroids, can solve the problems of limited application and the like

Inactive Publication Date: 2007-08-15
MITSUBISHI CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] Also, synthesis of cholesta-4,6,24-trien-3-one as an intermediate when using cholesta-5,7,24-trien-3β-ol as a raw material as various steroid medicines Intermediates are useful, but have historically been obtained from raw materials of natural origin and prepared through lengthy reaction steps, thus limiting their use in terms of cost and quantity

Method used

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preparation example Construction

[0235] The cholesta-5,7,24-trien-3β-ol used as a raw material in the production method of the present invention itself is a known substance. For example, it can be produced by, for example, metabolically engineering fungi that produce ergosterol via zymosterol, culturing the produced mutant strain, and collecting it from the culture. For details of the production method, for example, methods described in JP-A-5-192184 and JP-A-2004-141125 can be referred to.

[0236] Preparation of cholesta-4,7,24-triene-3 represented by the following formula (3) from cholesta-5,7,24-trien-3β-ol represented by the following formula (2) - Keto steps

[0237]

[0238] As can be seen from the above reaction formula, step 1 of the present invention is to simultaneously carry out the oxidation of the 3-position hydroxyl and the 5-position double bond of cholesta-5,7,24-triene-3β-alcohol (hereinafter sometimes referred to as "compound 2") A step toward the isomerization of the 4-position. Thi...

Embodiment 1

[0370]

[0371] 4.38g (11.47mmol) of cholesta-5,7,24-triene-3-ol (compound 2) and 11.24g (114.66mmol) of cyclohexanone were dissolved in 44ml of toluene, and the reduction was repeated several times at room temperature. After pressure degassing and nitrogen substitution, 1.17 g (5.74 mmol) of aluminum isopropoxide was added at room temperature, and the mixture was stirred at 112° C. for 2 hours under a nitrogen atmosphere. After the reaction, the reaction liquid was cooled to room temperature, 2.3ml of water was added and stirred at room temperature for 1 hour. The precipitated precipitate was filtered, the filtrate was concentrated, and it was separated and purified by silica gel column chromatography to obtain 4.01 g of cholesta-4,7,24-trien-3-one (compound 3). The yield of the isolated and purified compound 2 was 92%, and its NMR shift value (δppm) is shown below.

[0372] δ: 0.60(s, 3H, 18-H), 0.96(d, 6.5Hz, 3H, 21-H), 1.18(s, 3H, 19-H), 1.61(s, 3H, 26-H), 1.69 (s, 3H,...

Embodiment 2

[0374]

[0375] 3.49g (9.18mmol) of cholesta-4,7,24-triene-3-one (compound 3) obtained by the method of Example 1 was dissolved in 70ml of methanol, and several times of vacuum decompression were carried out at room temperature. After gas and nitrogen replacement, 2.53 g (38.40 mmol) of 85% granular potassium hydroxide was added, and the mixture was stirred at 64° C. for 7 hours under a nitrogen atmosphere. After the reaction, the reaction liquid was cooled to room temperature, 2.37 g of acetic acid was added and stirred at room temperature for 0.5 hours. Next, methanol was distilled off under reduced pressure, water was added, and extracted with ethyl acetate, the organic phase was washed with water, dried, concentrated, and separated and purified by silica gel column chromatography to obtain 3.13 g of cholestan-4,7,24- Trien-3-ones (Compound 4). The yield of isolated and purified compound 3 was 90%, and its NMR shift value (δppm) is shown below.

[0376] δ: 0.76(s, 3H, 1...

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Abstract

An object of the present invention is to provide a novel method for producing a steroid compound. The present invention provides a method for producing 3,7-dioxo-5beta-cholanic acid or ester derivatives thereof, which uses, as raw materials, sterols having double bonds at positions 5 and 24, such as cholesta-5,7,24-trien-3beta-ol, ergosta-5,7,24(28)-trien-3beta-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3beta-ol, and which comprises the following 4 steps: (I) a step of performing oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step of converting position 24 to a carboxyl group or an ester derivative thereof by the oxidative cleavage of a side chain; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5beta-configuration by reduction of a double bond at position 4.

Description

technical field [0001] The present invention relates to a method for preparing steroids, in particular, to a method for preparing 3,7-dioxo-5β-cholestanoic acid or its ester derivatives, which is obtained by adding a steroid with a double bond at the 4-position The compound is reductively saturated to carry out the construction of the 5β stereo. More specifically, it relates to a method for preparing 3,7-dioxo-5β-cholestanoic acid or its ester derivatives. The method is based on the 5-position and 24 Cholesta-5,7,24-trien-3β-ol, or ergosta-5,7,24(28)-trien-3β-ol, streptosterol or fucosterol of sterols with a double bond , Ergosta-5,24(28)-diene-3β-alcohol is raw material, and through following 4 steps, namely: [0002] (1) carry out the step of the oxidation of 3-position hydroxyl and the isomerization of 5-position double bond to 4-position; [0003] (II) a step of changing the 24-position into a carboxyl group or an ester derivative thereof by oxidative cleavage of the sid...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 竹原润藤原尚哉河井润也远藤恭子
Owner MITSUBISHI CHEM CORP
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