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Synthesis method of 3-oxetane acetic acid

A technology of oxetane and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of no literature report on compound synthesis methods, etc., and achieve the effects of avoiding product deterioration, reasonable route design, and high purity

Inactive Publication Date: 2017-04-19
TIANJIN YAO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no literature reporting the synthesis method of this compound

Method used

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  • Synthesis method of 3-oxetane acetic acid
  • Synthesis method of 3-oxetane acetic acid
  • Synthesis method of 3-oxetane acetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: small test experiment

[0023] first step:

[0024]

[0025] Table 1 Step one small test experimental feeding table

[0026] compound molecular weight Feeding amount relative molar mass Equivalent number 1 72 4g 0.056mol 1.1eq 2 410 20.7g 0.051mol 1.0eq THF - 80mL - -

[0027] The dosages of various compounds in this reaction are shown in Table 1.

[0028] Operation steps: Add compound 2 (20.7g) and THF (50mL) into a 250mL three-necked flask in sequence, drop the mixture of compound 1 (4g) and THF (30mL) into the system at 0-5°C, and stir at natural temperature After 5 hours, TLC (PE:EA=10:1) showed that the reaction of the starting material (Rf=0.1) was complete, and a product (Rf=0.3) was formed.

[0029] Post-processing: the above system was spin-dried, purified by column chromatography (PE:EA=20:1) to obtain the product point, and spin-dried to obtain compound 3 (8 g of white solid), with a yiel...

Embodiment 2

[0040] Embodiment 2: pilot test

[0041] first step:

[0042]

[0043] Table 3 Step 1 Pilot Test Feeding Table

[0044] compound molecular weight Feeding amount relative molar mass Equivalent number 1 72 40g 0.56mol 1.1eq 2 410 207g 0.51mol 1.0eq THF - 800mL - -

[0045] The dosages of various compounds in this reaction are shown in Table 3.

[0046] Operation steps: Add compound 2 (207g) and THF (500mL) into a 2L three-necked flask in turn, drop the mixture of compound 1 (40g) and THF (300mL) into the system at 0-5°C, and stir at natural temperature for 7 hours , TLC (PE:EA=10:1) showed that the reaction of the starting material (Rf=0.1) was completed, and a product (Rf=0.3) was formed.

[0047] Post-processing: the above system was spin-dried, purified by column chromatography (PE:EA=20:1) to obtain the product point, and spin-dried to obtain compound 3 (75 g of white solid), with a yield of 61%.

[0048] Step two: ...

Embodiment 3

[0056] Embodiment 3: scale-up experiment

[0057] first step:

[0058]

[0059] Table 5 Step 1 scale-up experiment feed list

[0060] compound molecular weight Feeding amount relative molar mass Equivalent number 1 72 200g 2.7mol 1.2eq 2 410 1.04kg 2.4mol 1.0eq THF - 3mL - -

[0061] The feeding amount of various compounds in this reaction is shown in Table 5.

[0062]Operation steps: Add compound 2 (1.04kg) and THF (2mL) into a 5L three-necked flask in turn, drop the mixture of compound 1 (200g) and THF (1L) into the system at 0-5°C, and stir at natural temperature for 10 After 1 hour, TLC (PE:EA=10:1) showed that the reaction of the starting material (Rf=0.1) was complete, and a product (Rf=0.3) was formed.

[0063] Post-processing: the above system was spin-dried, purified by column chromatography (PE:EA=20:1) to obtain the product point, and spin-dried to obtain compound 3 (420 g of white solid), with a yield of 68...

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Abstract

The invention belongs to the fields of organic synthesis and medicine synthesis, and especially relates to a synthesis method of 3-oxetane acetic acid. The synthesis method includes the following steps: (1) performing a reaction to 3-oxetanone and benzyloxycarbonylmethylene triphenylphosphine to obtain an intermediate product 2-(oxetane-3-yl-methylene)benzyl acetate; (2) performing hydrogenation debenzylation to the 2-(oxetane-3-yl-methylene)benzyl acetate to obtain the final product 3-oxetane acetic acid. The reactions in the method can be carried out just at room temperature and reaction conditions are easy to control. The final product can be obtained through re-crystallization and purification, so that the product is high in purity, and deterioration of the product during purification is avoided. The method has reasonable route design, simple process, high yield and short synthesis period, and can provide a high-purity raw material for a subsequent synthesis reaction sufficiently and timely.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and drug synthesis, and in particular relates to a synthesis method of 3-oxetaneacetic acid. Background technique [0002] 3-Oxetaneacetic acid is an important pharmaceutical intermediate, which can be widely used in the design of drug molecules. It has a small molecular weight and unique structure, and can be derived from a variety of downstream products, which has a wide range of uses. [0003] However, due to reasons such as high ambient temperature or poor storage sealing, the compound is easily deteriorated, so the compound cannot be stored stably for a long time. Therefore, when the intermediate is needed in the organic synthesis process, it is difficult to directly purchase the chemical reagent, and it can only be synthesized by itself, and it is fed into the next reaction in time after the synthesis. However, there is no literature reporting the synthesis method of this compound. [000...

Claims

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Application Information

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IPC IPC(8): C07D305/06
CPCC07D305/06
Inventor 陈冬恩贤少赟靳跃双
Owner TIANJIN YAO TECH CO LTD
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