A kind of synthetic method of Rieter mold metabolite 12
A technology of methyl phenyl and methoxyacetyl, applied in the field of synthesis of Rieter mold metabolite 12: N--N-alanine, achieved considerable application prospects and good recovery rate
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[0023] A synthetic method for metabolite 12 in Rieter mold, comprising the following steps:
[0024] 1) Take Lida mold (I) as the raw material drug, dissolve it in an organic solvent, add the catalyst dropwise after heating up, and then extract the reaction product with an organic solvent to obtain compound (II) after heating up again;
[0025] 2) Re-dissolving compound (II) in an alkaline substance and reacting at room temperature to obtain metabolite 12 (III).
[0026] The following are the reaction steps:
[0027]
Embodiment 1
[0031] Take by weighing 27.9g (100mmol) metalaxyl, put into there-necked bottle containing 200mL 55% pyridine aqueous solution, make it fully dissolve, and be heated to 70 degree, then add the potassium permanganate of 24g (150mmol) in batches, make it The process was kept at 70 overnight for reaction, the resulting liquid was filtered, and the filtrate was recovered, then the pH was adjusted to 2 with 6N HCl, extracted twice with 150 mL of ethyl acetate, the ethyl acetate layers were combined, dried with 2.5 g of anhydrous sodium sulfate, and then carried out Vacuum suction filtration, the filtrate recovered the solvent to obtain 15g of solid, which was separated by column chromatography, eluent PE:EA5:1---3:1, and 1.2g of compound (II) was obtained, namely N-(2-carboxy-6-methyl phenyl)-N-(methoxyacetyl)alanine methyl ester, the recovery rate was 5%.
[0032] Compound (II) was dissolved in 10 mL of methanol, 2 mL of 5N sodium hydroxide was added to the solution, and the react...
Embodiment 2
[0037] The purity of metabolites was identified by high performance liquid chromatography and nuclear magnetic analysis.
[0038] High-performance liquid chromatography: take 5 mg of sample and add acetonitrile to dissolve, and add a small amount of acetonitrile containing 0.1% trifluoroacetic acid dropwise, and inject 10 μL of sample. Chromatographic conditions: Waters Xbridge C18 column (4.6*250*5μm), mobile phase: acetonitrile / water=40 / 60 (v / v), flow rate: 1mL / min, detection wavelength: 220nm, temperature: 35°C.
[0039] NMR analysis method: Take 5 mg of the sample and add 0.5 mL of a suitable deuterated reagent, ultrasonic for 5 minutes, dissolve evenly and clarify, enter the NMR instrument, and scan the hydrogen spectrum 64 times.
[0040] The metabolite 8 obtained in Example 1 was detected by HNMR and HPLC respectively.
[0041] Among them, as attached figure 1 As shown, by HNMR detection, it can be seen that 1.12-1.14ppm (d, 3H, CH3 aliphatic methyl hydrogen) 2.16ppm an...
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