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PMS synthesis method

A synthesis method and technology of mixed solvents are applied in the field of PMS synthesis to achieve the effects of simple process, avoiding side reactions and mild conditions

Active Publication Date: 2021-02-09
HUBEI HUNTIDE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are almost no relevant reports on the synthesis of PMS. Sederma in France is the main supplier of PMS, and the large-scale production of PMS in China is still blank.

Method used

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  • PMS synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of N-palmitoyl-L-serine methyl ester

[0048] Add 100.0g L-serine methyl ester hydrochloride, 700.0g tetrahydrofuran, and 126.6g triethylamine to the four-necked flask successively, and stir at room temperature; then dissolve 176.6g palmitoyl chloride in 300g tetrahydrofuran, and slowly dropwise add A solution of the palmitoyl chloride in tetrahydrofuran. After dropping, stir the reaction at room temperature for 1-2 hours. After the reaction was completed, 2000 g of water was slowly added dropwise to the system to precipitate a large amount of white solid, which was collected by filtration to obtain 218.3 g of the product N-palmitoyl-L-serine methyl ester, with a yield of 95.5%.

Embodiment 2

[0049] Example 2: Synthesis of N-palmitoyl-O-benzyl-L-serine

[0050] Under continuous nitrogen purging, add 36.63g of sodium hydrogen (60% content) to the four-neck flask successively, add dropwise 655.0g of tetrahydrofuran, stir at room temperature, and slowly add 218.3g of N-palmitoyl-L-serine in batches at this temperature Methyl ester, stirred at room temperature for 0.5h to drive off the generated hydrogen. Then, under the protection of nitrogen, 152.3 g of benzyl bromide was added dropwise, and after the drop was completed, the reaction was stirred at room temperature for 1-2 hours. After the reaction is completed, add 488.4g of 10wt% aqueous sodium hydroxide solution dropwise to the system, and stir at room temperature for 3-5 hours. After the reaction is completed, adjust the pH to 3-4 with hydrochloric acid, and extract 3 times with ethyl acetate (100g*3). The organic layers were combined, concentrated to dryness under reduced pressure, and recrystallized from metha...

Embodiment 3

[0051] Example 3: Synthesis of N-palmitoyl-O-benzyl-L-serine tetradecyl ester

[0052] Add 243.6g N-palmitoyl-O-benzyl-L-serine, 600g dichloromethane, 2.05gDMF successively in the four-necked flask, stir at room temperature, drop 85.6g oxalyl chloride at this temperature, stir at room temperature and react 2- 3 hours. After the reaction was completed, the obtained acid chloride was set aside for use, and then 132.5 g of tetradecyl alcohol, 600.0 g of dichloromethane, and 85.3 g of triethylamine were added to another four-necked flask. Under nitrogen protection, the aforementioned acid chloride was added dropwise at room temperature, 1-2 After hours of dripping, continue to react for 2-3 hours. After the reaction was completed, it was washed with water (100g*3) for 3 times to obtain an organic layer, which was concentrated to dryness under reduced pressure to obtain the crude N-palmitoyl-O-benzyl-L-serine tetradecyl ester, which was directly For the next step, the yield is 10...

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Abstract

The invention discloses a PMS synthesis method, and belongs to the technical field of organic synthesis. The method comprises the following steps: reacting L-serine methyl ester hydrochloride with palmitoyl chloride to obtain N-palmitoyl-L-serine methyl ester; carrying out benzyl protection on the N-palmitoyl-L-serine methyl ester, and hydrolyzing the methyl ester to obtain N-palmitoyl-O-benzyl-L-serine; esterifying the N-palmitoyl-O-benzyl-L-serine and tetradecyl alcohol to obtain N-palmitoyl-O-benzyl-L-serine tetradecyl ester; and finally, debenzylating the N-palmitoyl-O-benzyl-L-serine tetradecyl ester to obtain the PMS. According to the invention, cheap L-serine methyl ester hydrochloride is used as a raw material, and benzyl is used for protecting hydroxyl, so that the side reaction of esterification with tetradecyl alcohol when the hydroxyl in a serine parent is not protected is effectively avoided, the reaction conversion rate is improved, the difficulty of separation and purification caused by byproducts is reduced, and the method can be effectively suitable for industrial mass production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of PMS. Background technique [0002] Ceramide, that is, N-ester acyl sphingosine, is a component of cell membranes, the basic unit of sphingomyelin, and an important biologically active substance in the body. And other functions, especially the special function of improving moisturizing make ceramide become a hot spot in cosmetics, and ceramide as an important lipid second messenger in the body has attracted the attention of researchers. Current studies have found that ceramide can activate a variety of protein kinases and Transcription factors participate in intracellular signal transduction, thereby affecting various physiological and pathological processes such as cell growth, proliferation, differentiation, apoptosis and injury. The development and application of ceramide is mainly added to cosmetics as a moisturizer. People also try to use natu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/47C07C231/12C07C231/02
CPCC07C231/12C07C231/02C07C233/47
Inventor 冯议吴伟伟李建雄汪黎明李海量唐启明
Owner HUBEI HUNTIDE BIOTECH
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