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Steroid ester preparation method

A technology of esterification and steroids, which is applied in the field of preparation of steroidal esterification, can solve problems such as poor quality, many impurities, and low product yield, and achieve the effects of simple operation, improved yield and quality, and improved purity

Active Publication Date: 2014-07-09
ZHEJIANG XIANJU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] However, DCC (N,N-dicyclohexylcarbodiimide) product DCU (N,N-dicyclohexyl urea) will remain in the product, which needs to be removed by the column method. At the same time, p-toluenesulfonic acid contains crystal water, When used as a catalyst, the reaction will produce more impurities, and the yield of the product obtained by this esterification method is not high, and the quality is relatively poor

Method used

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preparation example Construction

[0030] The preparation method of the steroidal esterification product of the present invention uses the alcoholic hydroxy steroidal compound (I) as the starting material, undergoes the catalysis of a catalyst, uses a dehydrating agent, and undergoes an esterification reaction with the alkanoic acid compound (II) to obtain the steroidal esterification compound (I) Body ester compound (III), its operational route is as follows:

[0031]

[0032] Wherein, R1 in the alcoholic hydroxysteroid compound (I) contains alcoholic hydroxysteroids such as hydrogen, alkanes, enynes, and ketones;

[0033] R2 in the alkanoic acid compound (II) includes C2-C18 alkanoic acids such as acetic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, undecanoic acid, and tridecanoic acid.

[0034] Specifically include the following steps:

[0035] In the first step, the alcohol hydroxy steroid compound (I) is put in, the reaction solvent is added, stirred, and the alkanoic acid compou...

Embodiment 1

[0042] Preparation of testosterone undecanoate:

[0043] Put 10g of steroidal alcohol testosterone into the reaction flask, add 200ml of reaction solvent chloroform, stir, add 20g of undecanoic acid, add 5g of catalyst DMAP and dehydrating agent N,N-diisopropylcarbodiimide (DIC ) 20g combination, reacted at 5-35°C for 5 hours, added water to terminate, put in 20g of alumina as an acid removal substance and stirred for 30 minutes; filtered, extracted, separated, combined and concentrated the organic phases to obtain the compound testosterone undecanoate; yield 155%, HPLC≧98%.

Embodiment 2

[0045] Preparation of norethindrone enanthate:

[0046] Put 10 g of steroid norethindrone into the reaction flask, add 200 ml of reaction solvent chloroform, stir, add 20 g of heptanoic acid, add 5 g of catalyst DMAP and dehydrating agent 1-ethyl-(3-dimethylaminopropyl) carbon Diimine hydrochloride (EDCI) 20g combination, react at 5-35°C for 5 hours, add water to terminate, add 20g calcium oxide as an acid removal substance and stir for 30 minutes; filter, extract, separate layers, combine organic phases and concentrate to obtain compound 11 Testosterone acid; yield 120%, HPLC≧98%.

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Abstract

The invention discloses a steroid ester preparation method. According to the preparation method, an alcoholic hydroxyl steroid compound (I) as a starting material generates an esterification reaction with an alkyl acid compound (II) by using a dehydrant after being subjected to the catalysis of a catalyst, so that a steroid ester (III) is obtained, and the process route is as shown in the specification, wherein the R1 in the alcoholic hydroxyl steroid compound (I) contains hydrogen, alkanes, ene-alkyne and ketone; the R2 in the alkyl acid compound (II) contains C2-C18 alkyl acids. By the combination of the novel dehydrant and the specific catalyst, the dehydrating problem in the esterification reaction can be solved, the reaction is moderate and complete, the operation is simple, the yield and the quality are enhanced greatly, and products have no dehydrant residue.

Description

technical field [0001] The invention relates to a chemical synthesis method of medicine, in particular to a preparation method of steroid esters. Background technique [0002] At present, for the preparation of steroidal esterification compounds, most manufacturers produce by the acid chloride method. "Synthesis of long-acting male hormone-testosterone undecanoate" disclosed in the 12th, 3rd, 127-128 of the Journal of Zhejiang Medical University in 1983; Synthesis of Several Testosterone Derivatives", "Preparation Method of Testosterone Enanthate" disclosed in Chinese Invention Patent 201210010447.8, these processes use alcohol hydroxysteroids as starting materials, anhydrous benzene as solvent, triethylamine as catalyst, (III) can be obtained by esterification with alkanoyl chloride, and the chemical reaction formula is as follows: [0003] [0004] R1 in the above formula includes hydrogen, alkanes, enynes, ketones and other alcohol hydroxy steroids, and R2 includes a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J75/00C07J1/00C07J7/00
Inventor 赵俊志艾荣华
Owner ZHEJIANG XIANJU PHARMA
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