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

Synthesis method of S-beta-hydroxy-gamma-butyrolactone

A synthesis method and technology of methyl hydroxybutyrate are applied in the field of synthesizing -β-hydroxy-γ-butyrolactone, which can solve the problems of high price, flammability, explosion, and difficulty in storage, and achieve the effect of low price

Inactive Publication Date: 2010-11-24
SHANGHAI INST OF TECH
View PDF2 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The synthesis route condition of this method is milder, and its limitation is that this route has adopted the borane dimethyl sulfide complex that is inflammable and explosive, is not easy to preserve, and is expensive, and the solvent used is anhydrous and oxygen-free tetrahydrofuran, which is harmful to Industrial production is extremely unfavorable

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
  • Synthesis method of S-beta-hydroxy-gamma-butyrolactone
  • Synthesis method of S-beta-hydroxy-gamma-butyrolactone
  • Synthesis method of S-beta-hydroxy-gamma-butyrolactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A kind of synthetic method of S-β-hydroxyl-γ-butyrolactone, comprises the steps:

[0048] (1), the synthesis of L-dimethyl malate

[0049] Acetyl chloride (10ml) was slowly added to methanol (300ml) at 0°C. After dropping, L-malic acid (26.8 g, 0.2 mol) was added, slowly raised to room temperature, and stirred for 12 h. Methanol was concentrated, the residue was dissolved in 250ml of ethyl acetate, the organic phase was washed with saturated sodium bicarbonate, water and saturated sodium chloride solution, dried and concentrated to obtain an intermediate. Dissolve the intermediate in 2.5ml THF, add tetrabutylammonium fluoride (1.0M, 0.6ml, 0.6mmol) dropwise at 0°C, stir the mixture at 0°C for 3 hours, dilute with 15ml ether, and chlorinate the organic phase with water and saturated Washed with sodium solution, dried and concentrated to obtain 27 g of colorless oily liquid with a yield of 92%.

[0050] [α] D 25 = -7.50 (c 3.45, MeOH);

[0051] 1 H NMR (CDCl 3 , 3...

Embodiment 2

[0064] A kind of synthetic method of S-β-hydroxyl-γ-butyrolactone, comprises the steps:

[0065] (1), the synthesis of L-dimethyl malate

[0066] Acetyl chloride (5ml) was slowly added to methanol (300ml) at 0°C. After dropping, L-malic acid (26.8 g, 0.2 mol) was added, slowly raised to room temperature, and stirred for 12 h. Methanol was concentrated, the residue was dissolved in 250ml of ethyl acetate, the organic phase was washed with saturated sodium bicarbonate, water and saturated sodium chloride solution, dried and concentrated to obtain an intermediate. Dissolve the intermediate in 2ml of THF, add tetrabutylammonium fluoride (1.0M, 0.5ml, 0.5mmol) dropwise at 0°C, stir the mixture at 0°C for 3 hours, dilute with 15ml of ether, and the organic phase with water and saturated sodium chloride The solution was washed, dried and concentrated to obtain 26.4 g of a colorless oily liquid with a yield of 90%.

[0067] [α] D 25 = -7.50 (c 3.45, MeOH);

[0068] 1 H NMR (CDC...

Embodiment 3

[0081] A kind of synthetic method of S-β-hydroxyl-γ-butyrolactone, comprises the steps:

[0082] (1), the synthesis of L-dimethyl malate

[0083] Acetyl chloride (10ml) was slowly added to methanol (500ml) at 0°C. After dropping, L-malic acid (26.8 g, 0.2 mol) was added, slowly raised to room temperature, and stirred for 12 h. Methanol was concentrated, the residue was dissolved in 250ml of ethyl acetate, the organic phase was washed with saturated sodium bicarbonate, water and saturated sodium chloride solution, dried and concentrated to obtain an intermediate. Dissolve the intermediate in 5ml of THF, add tetrabutylammonium fluoride (1.0M, 1.0ml, 1.0mmol) dropwise at 0°C, stir the mixture at 0°C for 3 hours, dilute with 15ml of ether, and the organic phase with water and saturated sodium chloride The solution was washed, dried and concentrated to obtain 26.7 g of a colorless oily liquid with a yield of 91%.

[0084] [α] D 25 = -7.50 (c 3.45, MeOH);

[0085] 1 H NMR (CD...

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

No PUM Login to View More

Abstract

The invention discloses a synthesis method of S-beta-hydroxy-gamma-butyrolactone, comprising the steps of: synthesis of L-dimethyl ester malate, synthesis of 3, 4-dihydroxybutyric acid methyl ester, synthesis of S-hydroxy-gamma-butyrolactone and the like.The synthesis method mainly adopts BiBr3 / hydroborate / lower alcohol reducing system to selectively reduce monoester into alcohol, so that borane dimethyl sulfide composite which is combustible and explosive, is not easily stored and has high price in the prior art is avoided being used. The synthesis method of the S-beta-hydroxy-gamma-butyrolactone is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing a compound, in particular to a method for synthesizing (S)-β-hydroxyl-γ-butyrolactone. Background technique [0002] S-β-hydroxy-γ-butyrolactone is a very important chiral pharmaceutical intermediate 1，2 , and its synthesis has attracted more and more attention from chemists. Traditional techniques mainly include: esterification by L-malate, reduction, cyclization 3-6 ; or by the oxidation of sugars such as: lactose, maltose 7-9 , and finally synthesized S-β-hydroxy-γ-butyrolactone. In the former method, most of the regioselectivity when the two ester groups are reduced is not high, and there are more impurities, resulting in a lower yield; the latter method also leads to product purification due to the complex by-products produced during the oxidation process. very difficult. Therefore, the above techniques are difficult to realize industrialization. [0003] [0004] The synthetic method of ...

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
IPC IPC(8): C07D307/33
Inventor 姚志艺蒋晟孙小玲徐颖珺
Owner SHANGHAI INST OF TECH
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