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Preparation method of N10-trifluoroacetyl pteroic acid

A technology of trifluoroacetyl pteroic acid and N10-, which is applied in the field of medicine and chemical industry, can solve the problems of high toxicity of trifluoroacetic anhydride, unfavorable large-scale production, long reaction time, etc.

Pending Publication Date: 2021-10-01
SUZHOU IBIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing preparation methods generally require the use of trifluoroacetic anhydride as a solvent. Due to the high toxicity of trifluoroacetic anhydride and the long reaction time, it is not conducive to large-scale production.

Method used

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  • Preparation method of N10-trifluoroacetyl pteroic acid
  • Preparation method of N10-trifluoroacetyl pteroic acid
  • Preparation method of N10-trifluoroacetyl pteroic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0023]

[0024] In a 500mL three-necked flask under the protection of inert gas, add 19.5g (50mmmol) instant pteroic acid (80% content), 200mL DMSO, stir well, then add 12.6g (60mmmol) trifluoroacetic anhydride, 20-25°C Stir in the dark for 12 hours, add the filtrate to a mixture of 300 mL ethyl acetate and 300 mL deionized water, stir evenly, and separate phases. Extract the organic phase with 100mL ethyl acetate once more, combine the organic phases, dry over anhydrous magnesium sulfate, filter, evaporate the filtrate to about 100mL under vacuum, stir to remove crystals, cool to 5°C, filter, rinse with 100mL cold ethyl acetate filter cake. The filter cake was vacuum-dried (protected from light) to remove the organic solvent to obtain a yellow solid as compound II, N 10 - Trifluoroacetyl pteroic acid 16.5g, yield 81%.

Embodiment 2

[0026]

[0027] In the 500mL three-neck flask under the protection of inert gas, add 9.75g (25mmmol) instant pteroic acid (content is 80%), add 7.8g (25mmmol) anhydrous pteroic acid, 200mL DMSO, stir evenly, then add 12.6g ( 60mmmol) trifluoroacetic anhydride, and stirred in the dark at 20-25°C for 12 hours, and the filtrate was added to a mixture of 300mL ethyl acetate and 300mL deionized water, stirred evenly, and phase-separated. Extract the organic phase with 100mL ethyl acetate once more, combine the organic phases, dry over anhydrous magnesium sulfate, filter, evaporate the filtrate to about 100mL under vacuum, stir to remove crystals, cool to 5°C, filter, rinse with 100mL cold ethyl acetate filter cake. The filter cake was vacuum-dried (protected from light) to remove the organic solvent to obtain a yellow solid as compound II, N 10 - Trifluoroacetyl pteroic acid 15.3g, yield 75%.

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Abstract

The invention provides a preparation method of N10-trifluoroacetyl pteroic acid. The preparation method comprises the following step: reacting a compound trifluoroacetic acid or trifluoroacetic anhydride or a mixed solution of the trifluoroacetic acid and the trifluoroacetic anhydride with instant pteroic acid or a mixture of the instant pteroic acid and anhydrous pteroic acid in a DMSO or DMF solvent to obtain the N10-trifluoroacetyl pteroic acid. The method is simple in process, trifluoroacetic anhydride is prevented from being used as a solvent, the reaction time is greatly shortened, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, in particular to a kind of N 10 - A process for the preparation of trifluoroacetyl pteroic acid. Background technique [0002] Due to its small molecular weight, non-immunogenicity and good stability, folic acid is beneficial to form chemical bonds with other groups. Folate has a high affinity for folate receptors expressed on the cell surface. Folate is absorbed by cells through the combination of folate receptors and folic acid. Although folate receptors are expressed at very low levels in most normal cells, they are expressed at high levels in a large number of cancer cells to meet the high folate demand of rapidly dividing cells under low folate conditions. Folate receptor (FR) is a glycosylphosphatidylinositol-coupled protein. Among them, FRα receptors are also expressed in low to moderate levels in normal tissues such as choroid plexus, placenta tissue, proximal r...

Claims

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Application Information

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IPC IPC(8): C07D475/04C07B59/00
CPCC07D475/04C07B59/002C07B2200/05
Inventor 黄保华许磊胡新礼戴建
Owner SUZHOU IBIO TECH CO LTD
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