Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Improved synthesis method of cosmetic active ingredient boehine

A technology of active ingredient and boson, which is applied in the field of improved synthesis of boson, an active ingredient in cosmetics, can solve the problems of increasing the difficulty of enlargement of the process, unable to control the reduction product, and difficult to completely react completely, and achieve a good reaction effect. , Improve the efficiency of process research and development, and reduce the effect of labor costs

Active Publication Date: 2021-12-10
上海昕凯医药科技有限公司
View PDF9 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In this method, sodium borohydride reduction is used, it is difficult to complete the reaction completely, and the reduction product of the required single configuration cannot be controlled, and finally the required S configuration is obtained by column chromatography.
[0009] In addition, in the traditional reactor reaction, the reaction will exotherm violently and produce a large amount of gas when feeding materials, which poses a great safety hazard, which increases the difficulty of process scale-up

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Improved synthesis method of cosmetic active ingredient boehine
  • Improved synthesis method of cosmetic active ingredient boehine
  • Improved synthesis method of cosmetic active ingredient boehine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Weigh 190g of 1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)propan-2-one and dissolve it in 1L of methanol, stir to dissolve, Then inject it into the preheating module and preheat to 70°C; set the palladium carbon filling volume to 5mL, the particle size to 0.5mm, and the pressure to 5atm, and then control the H 2 The feed flow rate is 30 sccm; N 2 The feed flow rate is 65 sccm, and finally the preheated 1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)propan-2-one solution Inject into the preheated reaction module at a feed flow rate of 0.8mL / min. Collect the effluent reaction solution (sampling test, nuclear magnetic external standard calculation contains 178g of product, TLC shows that the raw material is obviously left), spin dry the solvent methanol, beat with 480mL petroleum ether / 2-methyltetrahydrofuran (volume ratio 12 / 1) for 1h, and suction filter A white solid was obtained, and 162 g of the product was obtained by drying, the yield was 8...

Embodiment 2

[0034] Weigh 190g of 1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)propan-2-one and dissolve it in 1L isopropanol, stir to dissolve Then inject it into the preheating module and preheat to 70°C; set the loading amount of palladium carbon to 5mL, the particle size to 0.5mm, and the pressure to 5atm, and then control the H 2 The feed flow rate is 30 sccm; N 2 The feed flow rate is 65 sccm, and finally the preheated 1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)propan-2-one solution Inject into the preheated reaction module at a feed flow rate of 0.8mL / min. Collect the effluent reaction solution (sampling test, NMR external standard calculation contains 190g of product, TLC shows no raw material remaining), spin-dry the solvent isopropanol, 480mL petroleum ether / 2-methyltetrahydrofuran (volume ratio 12 / 1) mixed solvent beating for 1h , a white solid was obtained by suction filtration, and 188 g of product was obtained by drying, the yield was 98%, and th...

Embodiment 3

[0038]Weigh 190g 1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)propan-2-one and dissolve it in 500mL isopropanol, stir to dissolve Then inject it into the preheating module and preheat to 70°C; set the loading amount of palladium carbon to 5mL, the particle size to 0.5mm, and the pressure to 5atm, and then control the H 2 The feed flow rate is 30 sccm; N 2 The feed flow rate is 65 sccm, and finally the preheated 1-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)propan-2-one solution Inject into the preheated reaction module at a feed flow rate of 0.8mL / min. The effluent reaction solution was collected and sampled for detection. TLC showed that a large amount of raw materials remained, and the NMR external standard method estimated that it contained 106g of product, with a yield of 55%. The R / S configuration ratio after carbonyl reduction was 48 / 52.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
particle diameteraaaaaaaaaa
Login to View More

Abstract

The invention provides an improved synthesis method of a cosmetic effective component bose, and belongs to the field of organic synthesis. The preparation method comprises the following steps: dissolving 1-{(2S, 3R, 4S, 5R)-3, 4, 5-trihydroxytetrahydro-2H-pyran-2-yl} propan-2-one and BPh3 in isopropanol, then adding the mixture into a preheating module, and preheating the mixture to 60-70 DEG C; filling a palladium-carbon catalyst into a reactor, opening a hydrogen feeding valve and a nitrogen feeding valve, controlling the flow rate, adding the preheated raw material solution into a reaction module, carrying out gas-liquid-solid three-phase reaction, and carrying out treating to obtain a target product, namely the glassine. The catalyst used in the method provided by the invention can be recycled to save the cost, the reaction condition is mild, the reaction yield is high, the purity is high, the numerical control display operation is simple, and the safety is high.

Description

technical field [0001] The invention relates to an improved synthesis method of Bosein, an effective component of cosmetics, and belongs to the technical field of organic synthesis. Background technique [0002] Hydroxypropyltetrahydropyranotriol, also known as Bosein Pro-Xylane, not only moisturizes, but also enhances skin elasticity and resists skin aging. As the core ingredient of L'Oreal Group's anti-aging products, it is a xylose derivative with anti-aging effects. Its main chemical structure is: At present, there are two main methods for synthesizing Bosein in the literature: [0003] Method 1: Use Ru / C at 80°C and methanol solvent to carry out catalytic pressure reduction. The reaction equation is as follows: [0004] [0005] In this method, catalytic hydrogenation is a traditional gas-liquid-solid three-phase heterogeneous reaction. In order to ensure the full contact of the three phases, high temperature and high pressure (15atm) conditions are required, whic...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10
CPCC07D309/10Y02P20/584
Inventor 谭新刚
Owner 上海昕凯医药科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com