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Preparation method of N-fmoc-D-methionine-O-octanoyl-serine/threonine

The technology of fluorene methoxycarbonyl and fluorene methoxycarbonyl- is applied in the field of preparation of serine/threonine derivatives, which can solve the problems of difficult operation, unenvironmental protection, and difficulty in purification, and achieve the effect of process stability.

Inactive Publication Date: 2019-04-16
GL BIOCHEM SHANGHAI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of N-fluorenylmethoxycarbonyl-O-octanoyl-serine / threonine, which mainly solves the difficulty in the operation of the existing synthesis method, and it is difficult to purify and unenvironmentally friendly in the scale-up production. technical problem

Method used

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  • Preparation method of N-fmoc-D-methionine-O-octanoyl-serine/threonine
  • Preparation method of N-fmoc-D-methionine-O-octanoyl-serine/threonine

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Embodiment 1

[0012] Step 1: Dissolve 20g (0.048mol) of N-fluorenylmethoxycarbonyl-L-serine-benzyl ester in 260ml tetrahydrofuran until dissolved. Then add 11.2g (0.0776mol) of n-octanoic acid, cool down to 0 degrees Celsius in an ice-water bath, slowly add 9.78g (0.0776mol) of N,N'-diisopropylcarbodiimide dropwise, and drop N,N'- For diisopropylcarbodiimide, remove the ice-water bath, let it slowly rise to 25 degrees Celsius, and react overnight. The next day, after thin-layer chromatography analysis, the raw material N-fluorenylmethoxycarbonyl-L-serine-benzyl ester had completely reacted and could be processed. Treatment: Suction filter the liquid, slowly evaporate the tetrahydrofuran to dryness at 35 degrees Celsius to obtain an oily substance, dissolve the oily substance with 400ml ethyl acetate, wash the ethyl acetate phase twice with citric acid with a concentration of 5% by mass, After that, it was washed three times with water until pH = 7, washed once with brine, and dried over an...

Embodiment 2

[0015] Step 1: Dissolve 20g (0.048mol) of N-fluorenylmethoxycarbonyl-DL-serine-benzyl ester in 260ml tetrahydrofuran until dissolved. Then add 11.2g (0.0776mol) of n-octanoic acid, 1.2g (0.0098mol) of 1-hydroxybenzotriazole, cool down to 0 degrees Celsius in an ice-water bath, and add 15.8g of N,N'-dicyclohexylcarbodiimide in batches (0.0776mol), after adding N,N'-dicyclohexylcarbodiimide, remove the ice-water bath, let it slowly rise to 25 degrees Celsius, and react overnight. The next day, after thin-layer chromatography analysis, the raw material N-fluorenylmethoxycarbonyl-DL-serine-benzyl ester had completely reacted and could be processed. Treatment: Cool down to 0°C to obtain the liquid, evaporate the tetrahydrofuran to dryness at 35°C to obtain an oily substance, dissolve the oily substance with 400ml of ethyl acetate, wash the ethyl acetate phase twice with 5% citric acid by mass , washed twice with water until pH = 7, washed once with brine, and dried over anhydrous ...

Embodiment 3

[0018] Step 1: Dissolve 20g (0.048mol) of N-fluorenylmethoxycarbonyl-Dserine-benzyl ester in 260ml tetrahydrofuran until dissolved. Add 11.2 g (0.0776 mol) of n-octanoic acid, cool down to 0 degrees Celsius in an ice-water bath, add 14.7 g of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride in batches, and complete the addition 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, remove the ice-water bath, let it slowly rise to 25 degrees Celsius, and react overnight. The next day, after thin-layer chromatography analysis, the raw material N-fluorenylmethoxycarbonyl-D serine-benzyl ester had completely reacted and could be processed. Treatment: Suction filter the liquid, slowly evaporate the tetrahydrofuran to dryness at 35 degrees Celsius to obtain an oily substance, dissolve the oily substance with 400ml ethyl acetate, wash the ethyl acetate phase twice with citric acid with a concentration of 5% by mass, After that, it was washed three times with water unti...

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Abstract

The invention relates to a preparation method of N-fmoc-D-methionine-O-octanoyl-serine / threonine, the preparation method mainly solves the technical problems that a prior synthetic method is difficultto operate, environmental protection cannot be ensured in purification and enlargement production. According to the technical scheme: the preparation method includes the following steps of: using N-fmoc-D-methionine-serine / threonine-benzyl ester as a starting material, carrying out condensation reaction with n-octanoic acid by adding a condensing agent to obtain N- fmoc-D-methionine-O-octanoyl-serine / threonine-benzyl ester, purifying, adding the N- fmoc-D-methionine-O-octanoyl-serine / threonine-benzyl ester in a debenzyl reagent to remove the benzyl through palladium carbon hydrogenation toobtain the N-fmoc-D-methionine-O-octanoyl-serine / threonine. The product has important application in the field of polypeptide medicine.

Description

technical field [0001] The invention relates to a preparation method of a serine / threonine derivative, especially a preparation method of N-fluorenylmethoxycarbonyl-O-octanoyl-serine / threonine. Background technique [0002] In the molecular structure of N-fluorenylmethoxycarbonyl-O-octanoyl-serine / threonine, there is a hydrophobic long carbon chain group - octanoyl, which plays an important role in constructing the spatial structure of active polypeptides. The industrial synthesis method has not been recorded in the literature. Du Xiumin. Preparation of Fmoc Series Protected Amino Acids. "China Excellent Master's Dissertations Full-text Database". 2005, page B014-73. React with N-fluorenylmethoxycarbonyl-serine / threonine (such as Fmoc-Ser-OH) to generate N-fluorenylmethoxycarbonyl-O-octanoyl-serine / threonine (such as Fmoc-Ser(n-Octanoyl )-OH), we tried this reaction, but there were too many miscellaneous points in the latter step, which was difficult to handle, and the octa...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C271/22
CPCC07C269/06C07C2603/18C07C271/22
Inventor 徐红岩奚文波戴健卢强熙秦丽星周志国
Owner GL BIOCHEM SHANGHAI
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