Preparation method of optically pure dextro cloprostenol sodium

A kind of dextro-cloprostol, optical technology, applied in the preparation field of d-cloprostol sodium, can solve the problem of no preparation method of d-cloprostol sodium and the like

Active Publication Date: 2015-04-15
宁波第二激素厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But also do not have a kind of preparation method of optically pure dexcloprostinol sodium so far

Method used

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  • Preparation method of optically pure dextro cloprostenol sodium
  • Preparation method of optically pure dextro cloprostenol sodium
  • Preparation method of optically pure dextro cloprostenol sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Step (1). Preparation of nortricyclic dimethyl ester:

[0075]

[0076] Put 31g of paraformaldehyde (dried at 60°C for 1h and finely ground) into a 1000ml three-necked bottle, add 500ml (98%) of formic acid and 4ml (98%) of sulfuric acid. Add 92g of 2,5-norbornadiene dropwise at 25°C, the internal temperature must not exceed 30°C, the solution turns brownish black after 17 hours of reaction, remove formic acid by distillation under reduced pressure at 70°C, and wash the residue with sodium bicarbonate aqueous solution until neutral , TLC detection. The product nortricyclic dimethyl ester in reaction formula (1) is made, and the product is liquid, and the yield is 65%.

[0077] Step (2). Preparation of keto acid:

[0078]

[0079] Add 3000ml of acetone and nortricyclodimethyl ester (all the nortricyclodimethyl ester prepared in step (1)) into a 5000ml three-necked flask, cool to 9°C, add 9ml of Jones oxidant dropwise, and control the reaction temperature at about...

Embodiment 2-4

[0141] The detailed method of Embodiment 2-4 is the same as that of Embodiment 1, except that some parameters are changed, and the above chemical reaction can be completed, and the detailed parameter changes are shown in the table below.

[0142] Specific implementation parameter table

[0143]

[0144]

[0145] The following abbreviations are used in this document:

[0146] R-: right-handed

[0147] TLC: thin layer chromatography

[0148] THF: Tetrahydrofuran

[0149] DIBAL-H: Diisobutylaluminum hydride

[0150] HPLC: High Performance Liquid Chromatography

[0151] Mp: melting point

[0152] bp: boiling point

[0153] Jones oxidizing agent: solution of chromium trioxide in concentrated sulfuric acid

[0154] PTS: p-toluenesulfonic acid.

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Abstract

The invention relates to a preparation method of optically pure dextro cloprostenol sodium. The method comprises the following steps: using the combination of ketonic acid and S-phenylethylamine resolving agent, and carrying out chiral resolution to obtain S-propenylphosphonate with the structural formula of R-ketonic acid; then separating to obtain R-chlorone and preparing to obtain R-cloprostenol sodium. The preparation method has the benefits that the optically pure dextro cloprostenol sodium in the invention is called D-cloprostenol sodium for short, the using amount only needs one third of cloprostenol sodium being a racemic modification in current market, and the pesticide effect is obviously better than cloprostenol sodium with three times of using amount.

Description

technical field [0001] The invention relates to a preparation method of sodium cloprostinol, in particular to a preparation method of optically pure d-cloprostinol sodium. Background technique [0002] The cloprostenol sodium and its injection contained in the 2010 edition of the Chinese Veterinary Pharmacopoeia, which is the product commonly used in Chinese pastures, is a racemate, and the product is composed of a pair of enantiomers: one is L-cloprostinol Sodium; the second is R-chloroprostol sodium. L-cloprostinol sodium is not only invalid, but also affects the performance of R-cloprostinol sodium drug effect. Optically pure sodium R-chloroprostol, that is, sodium R-chloroprostol, as a single enantiomer, only needs about one-third of the dosage of the racemate, and its pharmacokinetics is similar to that of the racemate. Basically the same, so it is safer and more effective. But so far there is no preparation method of optically pure dexcloprostinol sodium. Contents...

Claims

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Application Information

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IPC IPC(8): C07C405/00
Inventor王凯林
Owner宁波第二激素厂