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Precursors of novel PET (polyethylene terephthalate) precursor-fluoride standard ML-10 and preparation method thereof

A substance, a technology of diethyl methylmalonate, applied in the field of ML intermediates and their preparation, can solve problems such as restricting development

Inactive Publication Date: 2014-02-26
JIANGSU HUAYI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the deficiencies of existing technologies limit the development of this direction.

Method used

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  • Precursors of novel PET (polyethylene terephthalate) precursor-fluoride standard ML-10 and preparation method thereof
  • Precursors of novel PET (polyethylene terephthalate) precursor-fluoride standard ML-10 and preparation method thereof
  • Precursors of novel PET (polyethylene terephthalate) precursor-fluoride standard ML-10 and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0042] Specific embodiment 1, the structure and synthesis of material 4 and material 5, such as image 3 , Figure 4 , Figure 5 , Figure 6 shown.

[0043] Synthesis of Substance 1:

[0044] Under nitrogen protection, add 4g PPTS (pyridinium p-toluenesulfonate 16mmol, 0.2eq), 13.36g 5-bromo-1-pentanol (80mmol) and 200ml dichloromethane into a 500ml three-neck flask, dropwise add 10.08g3,4 - A solution of dihydropyran (120 mmol, 1.5 eq) in 200 ml of dichloromethane. After dropping, react overnight at room temperature. Stop the reaction, wash with water, dry the organic phase with anhydrous magnesium sulfate, filter to obtain the crude product m=25g, and separate the crude product through a 300-400 mesh silica gel column (ethyl acetate:n-hexane=5:1-2:1). The pure product m=13.7g was obtained, and the yield was 68%.

[0045] LC-MS[M+1] + =251 (100%), 253 (97%)

[0046] 1 HNMR (300MHz, CDCl 3):δ=4.55-4.60 (m, 1H), 3.81-3.92 (m, 1H), 3.69-3.80 (dt, 1H, J=6.4Hz, 9.7Hz), ...

specific Embodiment 2

[0081] Synthesis of Substance 1:

[0082] Under nitrogen protection, add 3-5g PPTS (pyridinium p-toluenesulfonate), 12-16g 5-bromo-1-pentanol and 200ml dichloromethane into a 500ml three-necked flask, drop 10-16g 3,4-dihydropyridine A solution of 200ml dichloromethane. After dropping, react overnight at room temperature. Stop the reaction, wash with water, dry the organic phase with anhydrous magnesium sulfate, filter to obtain the crude product, and separate the crude product through a 300-400 mesh silica gel column (ethyl acetate:n-hexane=5:1-2:1). Obtain pure product, productive rate 68%.

[0083] Table 1. Material 1 Synthesis Feeding Example

[0084] serial number

PPTS

5-Bromo-1-pentanol

Dichloromethane

3,4 dihydropyran

product

Yield

1

3g

12g

200ml

10g

13.7

68%

2

4g

14g

200ml

14g

15.8

68%

[0085] 3

5g

16g

200ml

16g

18.3

68%

...

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Abstract

The invention specifically relates to precursors of novel PET (polyethylene terephthalate) precursor-fluoride standard ML-10 and a preparation method thereof, namely 5-methylsulfonyl pentyl-2-diethyl methylmalonate, 5-toluenesulfonyl pentyl-2-diethyl methylmalonate and preparation methods of the 5-methylsulfonyl pentyl-2-diethyl methylmalonate and the 5-toluenesulfonyl pentyl-2-diethyl methylmalonate. The precursors, namely 5-methylsulfonyl pentyl-2-diethyl methylmalonate (substance 4) and 5-toluenesulfonyl pentyl-2-diethyl methylmalonate (substance 5) are synthesized by the following reaction of four steps totally under mild reaction conditions by taking 5-bromo-1-pentanol PPTS (pyridinium paratoluenesulfonate) as a reaction initiator: performing 1) the reaction of substituting a hydroxyl by a dihydropyran ring, 2) the reaction of substituting bromine by a methyl diethyl malonate group, 3) the hydrolysis reaction of the dihydropyran ring, and 4) the reaction of substituting the hydroxyl by a methllyl sulfonate group and p-toluenesulfonyl. The substance 4 and the substance 5 synthesized by the preparation method do not have related reports in the existing literature, and moreover, the stability of the substance 5 is very high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to the field of a class of ML intermediates and preparation methods thereof. Background technique [0002] PET utilizes nuclide labeling of positron emitters, such as some physiologically required compounds or metabolic substrates such as glucose, fatty acids, amino acids, receptor ligands, and water, etc. image. It has received extensive clinical attention for its ability to display the metabolic activity of organs or tissues and the function and distribution of receptors, also known as "in vivo biochemical imaging". It can be said that the emergence of PET has brought medical imaging technology to a new level, enabling non-invasive, dynamic and quantitative evaluation of the physiological and biochemical changes of cell metabolism in living tissues or organs under physiological conditions and during disease processes. Information at the molecular level is made possibl...

Claims

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Application Information

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IPC IPC(8): C07C309/73C07C309/65C07C303/28C07C55/32C07C27/02
Inventor 桂媛徐志红李新良高云虎
Owner JIANGSU HUAYI TECH
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