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Carboprost tromethamine related impurity L-amyl 15-ketone and preparation method thereof

A technology of pentyl and triphenylphosphine, which is applied in the field of compound preparation to achieve the effects of high yield, high safety and high purity

Pending Publication Date: 2020-12-25
NORTHEAST PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

L-amyl 15-ketone is a key impurity in L-amyl 15-ketone, and the above-mentioned impurities and their synthesis methods have not been retrieved at present. Therefore, developing a preparation method for L-amyl 15-ketone is a new task to be solved urgently

Method used

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  • Carboprost tromethamine related impurity L-amyl 15-ketone and preparation method thereof
  • Carboprost tromethamine related impurity L-amyl 15-ketone and preparation method thereof
  • Carboprost tromethamine related impurity L-amyl 15-ketone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 57.0g of methyltriphenylphosphine bromide and 300ml of tetrahydrofuran into a 1L four-neck flask, stir and cool down to -20°C to -15°C under nitrogen protection, and add 76.8ml of 2.5M n-butyllithium dropwise (the dropwise addition is completed in 30 minutes ), carry out the dehydrogenation reaction for 2 hours after the addition, maintain the temperature range of -20°C to -15°C, add 27.5g of ethyl valerate dropwise, continue the reaction for 3h after the addition, add 240ml of water to quench the reaction, separate liquid, water Layer was extracted twice with 200ml of ethyl acetate, the organic layers were combined, washed with 200ml of saturated sodium chloride, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was concentrated under reduced pressure to obtain an oil, which was left to precipitate a solid, and isopropyl ether was added 200ml of slurry was beaten for 2 hours, suction filtered, the filter cake was washed with 50ml of isopro...

Embodiment 2

[0037] Add 57.0g of methyltriphenylphosphine bromide and 300ml of tetrahydrofuran into a 1L four-neck flask, stir and cool down to -20°C to -15°C under nitrogen protection, and add 76.8ml of 2.5M n-butyllithium dropwise (the dropwise addition is completed in 30 minutes ), carry out the dehydrogenation reaction for 2 hours after the addition, maintain the temperature range of -20°C to -15°C, add 27.5g of ethyl valerate dropwise, continue the reaction for 3h after the addition, add 240ml of water to quench the reaction, separate liquid, water layer was washed twice with 200ml of ethyl acetate for extraction, the organic layers were combined, washed with 200ml of saturated sodium chloride, dried over anhydrous sodium sulfate, filtered with suction, the filtrate was concentrated under reduced pressure to obtain an oily substance, which was left to precipitate a solid, and isopropyl ether was added 200ml was beaten for 2h, suction filtered, the filter cake was washed with 50ml of is...

Embodiment 3

[0041] Add 57.0 g of methyltriphenylphosphine bromide and 300 ml of tetrahydrofuran into a 1L four-neck flask, stir and cool down to -20°C to -15°C under nitrogen protection, and add 22.0g of potassium tert-butoxide in batches (the addition is completed in 30 minutes), After the addition, carry out the dehydrogenation reaction for 2 hours, maintain the temperature range of -20°C to -15°C, add 27.5g of ethyl valerate dropwise, continue the reaction for 3h after the addition, add 240ml of water to quench the reaction, separate the liquid, and use the water layer Wash 2 times with 200ml of ethyl acetate for extraction, combine the organic layers, wash with 200ml of saturated sodium chloride, dry with anhydrous sodium sulfate, filter with suction, concentrate the filtrate under reduced pressure to obtain an oil, place it to precipitate a solid, add 200ml of isopropyl ether for beating After 2 hours, filter with suction, wash the filter cake with 50 ml of isopropyl ether, and dry to...

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Abstract

The invention relates to a carboprost tromethamine related impurity L-amyl 15-ketone and a preparation method thereof. The preparation method comprises the following steps of: (1) in the presence of afifth organic solvent, carrying out dehydrogenation reaction on methyl triphenyl phosphine halide by using strong base, adding ethyl valerate after reaction for a certain time, continuously reactingfor a certain time to obtain 1-triphenylphosphine 2-hexanone; and (2) carrying out wittig reaction on the 1-triphenylphosphine 2-hexanone obtained in the step (1) and a second organic solvent solutionof benzoyl corey lactone aldehyde to obtain a pentyl-15 ketone crude product. The method has the advantages of simple and convenient operation, high safety, and high yield and purity of an obtained product under optimal conditions, and can meet the requirements for impurity research.

Description

technical field [0001] The invention relates to a carboprost trometamol related impurity L-pentyl 15-one in the field of compound preparation and a preparation method thereof. Background technique [0002] Carboprost tromethamine is a tromethamine salt containing the (15S)-15 methyl derivative of the natural prostaglandin F2α, with the chemical name 7-{3α,5α-dihydroxy-2β[(3S)- 3-Hydroxy-3-methyl-trans-1-octene]-1α-cyclopentyl}-cis-5-heptenoic acid compound-2-amino-2-(hydroxymethyl)-1,3-propanediol , English name: 7-(3α,5α-dihydroxy-2β-[(3S)-3-hydroxy-3-methyl-trans-1-octenyl]-1α-cyclopentyl]-cis-5-heptenoic acid compound with 2-amino- 2-(hydroxymethyl)-1,3-propanediol. Molecular formula: C 25 h 47 NO 8 , molecular weight 489.64. [0003] Early postpartum hemorrhage is the main cause of perinatal complications and increased mortality, and it is also one of the serious complications of obstetrics. When the puerpera is combined with advanced age, multiple pregnancy, macro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/935
CPCC07D307/935
Inventor 张卫军李洋王玉军白洁韩晓丹刘素娜董爱军唐诗瑶
Owner NORTHEAST PHARMA GRP
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