A kind of preparation method of carboxylate compound
A technology of carboxylate compounds and carboxylic acid compounds, which is applied in the field of synthesis of methyl carboxylate compounds, can solve the problems of harsh reaction conditions, narrow substrate range, and pre-activation of raw materials, and achieve simple reaction system and convenient handling and operation , The effect of high atom economy
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Embodiment 1
[0035]
[0036] Add drug molecule 1a (Naproxen) (0.5 mmol, 115.2 mg) and methanol containing 40 mol% tert-butyl nitrite to the reaction test tube in sequence (methanol is 2 mL, tert-butyl nitrite is 0.2 mmol, the same as in the following examples); Then react under the condition of 40 ℃ in the air for 48 hours; after the reaction is finished, add sodium thiosulfate to stir and quench, then remove the solvent with a rotary evaporator, adsorb on silica gel, and finally use a mixed solvent of ethyl acetate and sherwood oil (1 : 1) The product 3a was obtained by column chromatography with a yield of 95% (separated yield). The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
[0037] 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 – 7.68 (m, 3H), 7.45 – 7.43 (m, 1H),7.20 – 7.11 (m, 2H), 3.93 – 3.86 (m, 4H), 3.69 (s, 3H), 1.62 (d, J = 7.2 Hz,3H); 13 C NMR (100 MHz, CDCl ...
Embodiment 2
[0040]
[0041] Add drug molecule 1a (Naproxen) (0.5 mmol, 115.2mg) and methanol containing 40mol% tert-butyl nitrite to the reaction test tube in sequence; then react for 48 hours at 25°C in air; after the reaction, add sulfur Sodium sulfate was stirred and quenched, and then the solvent was removed by a rotary evaporator, adsorbed on silica gel, and finally column chromatography was performed with a mixed solvent of ethyl acetate and petroleum ether (1:1) to obtain the product 3a with a yield of 63%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
Embodiment 3
[0043]
[0044] Add drug molecule 1b (Carprofen) (0.5 mmol, 136.9mg) and methanol containing 40mol% tert-butyl nitrite to the reaction test tube in turn; then react at 40°C in air for 48 hours; after the reaction, add sulfur Stir and quench with sodium sulfite, remove the solvent with a rotary evaporator, adsorb on silica gel, and finally perform column chromatography with a mixed solvent of ethyl acetate and petroleum ether to obtain the product 3b with a yield of 90%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
[0045] 1 H NMR (400 MHz, CDCl 3 ) δ 8.28 (s, 1H), 7.96 (d, J = 2.0 Hz, 1H), 7.91(d, J = 8.1 Hz, 1H), 7.34 – 7.29 (m, 2H), 7.25 – 7.21 (m, 1H), 7.18 (dd, J =8.1, 1.4 Hz, 1H), 3.90 (q, J = 7.2 Hz, 1H), 3.72 (s, 3H), 1.61 (d, J = 7.2Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 175.5, 140.3, 139.0, 138.0, 125.7, 124.7,124.1, 121.5, 1...
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