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A kind of method for preparing carboxylate compound

A carboxylic acid ester compound and a technology for carboxylic acid compounds, which are applied in the preparation of organic compounds, the preparation of carboxylic acid esters, chemical instruments and methods, etc., can solve the problems of easy decomposition of raw materials, complex reaction conditions, harsh reaction conditions, etc. Prospects for pharmaceutical and industrial applications, good functional group compatibility, mild reaction conditions

Active Publication Date: 2021-08-27
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Most of the currently reported methods for synthesizing esters have the following disadvantages: the raw materials need to be preactivated, the reaction conditions are harsh, the substrates used are harmful to the environment, the catalysts used are noble metals or heavy metals, the price is relatively expensive, the substrate range is narrow, and the atom economy is low. Poor; more importantly, because the general drug molecule has multiple functional groups, including sensitive functional groups, and the traditional esterification method has poor functional group tolerance, the traditional esterification method is generally not suitable for the esterification of drug molecules
However, the reaction requires the use of expensive and complex palladium-containing catalysts, and the reaction conditions are relatively complicated, the substrate range is narrow, and the raw materials used are easy to decompose, and the price is generally several times that of the corresponding carboxylic acid.

Method used

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  • A kind of method for preparing carboxylate compound
  • A kind of method for preparing carboxylate compound
  • A kind of method for preparing carboxylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] The drug molecule 1a (Naproxen) (0.5 mmol, 115.2 mg) was sequentially added to the reaction tube, which contained ethanol containing tert-butyl nitrite (2 ml of ethanol, nitrite was 0.5 mmol, and the following examples) Then, then reacted at 80 ° C in the air for 48 hours; after the reaction, sodium thiosulfate was stirred, and then the solvent was removed by a rotary evaporator, silica gel adsorbed, and finally using acetate and petroleum ether. The product 3a was obtained from the column layers, and the yield was 74%, and the yield was separated. The main test data of the product produced is as follows, and the actual synthetic product is consistent with theoretical analysis by analysis.

[0035] 1 H NMR (400 MHz, CDCL 3 δ 7.75 - 7.68 (m, 3H), 7.45 - 7.43 (m, 1H), 7.19 - 7.12 (M, 2H), 4.22 - 4.91 (S, 3H), 3.86 (Q, J = 7.2 Hz, 1H), 1.60 (D, J = 7.2 Hz, 3H), 1.22 (T, J = 7.2 Hz, 3h); 13 C NMR (100 MHz, CDCL 3 δ 174.5, 157.5, 135.7, 133.6, 129.1, 128.8, 118.8, 125...

Embodiment 2

[0038]

[0039] The drug molecule 1a (Naproxen) (0.5 mmol, 115.2 mg) was sequentially added to the reaction tube, containing ethanol of tert-butyl nitrite in 1 equivium nitrite; then reacted at 60 ° C in the air for 48 hours; after the end, after the end of the reaction Sodium sulfate was stirred, and then the solvent was removed by a rotary evaporator, silica gel adsorption, and finally the column chromatography was performed with a mixed solvent of ethyl acetate and petroleum ether. The yield was 60%. The main test data of the product produced is as follows, and the actual synthetic product is consistent with theoretical analysis by analysis.

Embodiment 3

[0041]

[0042] The drug molecule 1b (Naproxen) (0.5 mmol, 115.2 mg) was sequentially added to the reaction tube, and propanol of tert-butyl nitrite was contained; then the reaction was reacted at 80 ° C in the air for 48 hours; after the reaction, sulfur Sodium sulfate was stirred, and then the solvent was removed by a rotary evaporator, silica gel adsorption, and finally the mixed solvent of ethyl acetate and petroleum ether was subjected to column 3b, and the yield was 72%. The main test data of the product produced is as follows, and the actual synthetic product is consistent with theoretical analysis by analysis.

[0043] 1 H NMR (400 MHz, CDCL 3 δ 7.74 - 7.66 (M, 3H), 7.44 - 7.41 (m, 1H), 7.17 - 7.10 (M, 2H), 4.04 (T, J = 6.7 Hz, 2H), 3.91 (S, 3H), 3.86 (Q, J = 7.2Hz, 1H), 1.63 - 1.58 (M, 5H), 0.86 (T, J = 7.4 hz, 3h); 13 C NMR (100 MHz, CDCL 3 δ 174.7, 157.6, 135.9, 133.6, 129.3, 125.9, 118.9, 105.6, 66.3, 55.3, 45.5, 21.9, 18.5, 10.3; HRMS (ESI-TOF): anal.calcd. for c 17...

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Abstract

The invention relates to a method for preparing carboxylate compounds. Under the catalysis of nitrite, carboxylic acid and alcohol react in air to obtain ester compounds; the alcohol is ethanol, propanol or trifluoroethanol. The invention has the advantages of mild reaction conditions, abundant sources of raw materials, wide applicability of reaction substrates, simple and convenient operation, etc., and can modify a series of carboxylic acids with pharmaceutical properties and aliphatic carboxylic acids such as biologically active amino acids.

Description

Technical field [0001] The present invention relates to the field of carboxylate synthesis, and more particularly to a method of synthesizing a methyl ester compound of a carboxylate. Background technique [0002] The currently reported synthetic ester has the following disadvantages: the raw material requires pre-living, the reaction conditions are harsh, the substrate used is harmful to the environment, the catalyst used is precious metal or heavy metals, the price is more expensive, the base range is narrow, the atomic economy is more Difference; more importantly, since a general drug molecule has a plurality of functional groups, including sensitive functional groups, conventional esterification methods are poor tolerance, and therefore conventional esterification methods are generally not suitable for drug molecules. E.g: [0003] (1) Esterification of acid catalyzed carboxylic acid and alcohol is a classic method of synthetic esters, but the acid will damage the equipment, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/08C07C69/734C07D209/28C07D231/56C07C231/12C07C233/63C07D313/12B01J31/02
CPCC07C67/08C07C69/734C07D209/28C07D231/56C07C231/12C07C233/63C07D313/12B01J31/0235B01J31/0271C07C2601/14B01J2231/49
Inventor 万小兵郑永高陶苏艳李星星成雄略
Owner SUZHOU UNIV