A kind of chiral derivatization reagent and its preparation method and application
A technology for derivatization reagents and chiral compounds, applied in the field of chiral derivatization reagents and their preparation, can solve the problems of slow dissociation rate, inability to effectively analyze aromatic amine chiral substances, etc., and achieve chemical shift discrimination. The effect of large, simple and easy experimental operation, and easy access to raw materials
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[0052] The present invention also provides a preparation method of a chiral derivatizing reagent represented by formula (I), comprising the following steps:
[0053] Dissolving the first compound in ethanol, the first compound is selected from any of 2-fluoro-4-nitrobenzaldehyde, 3-fluoro-5-nitrobenzaldehyde, and 4-fluoro-3-nitrobenzaldehyde One; the second compound is dissolved in deionized water, and the second compound is selected from trans-4-fluoro-L-proline, cis-4-fluoro-L-proline, trans-4- any one of fluoro-D-proline or cis-4-fluoro-D-proline;
[0054] The molar ratio of the first compound and the second compound is less than 1.0, the two are mixed, the pH of the mixed solution is adjusted to 10-10.5, and the reaction is carried out at room temperature for 15 min to obtain the formula (I). A chiral derivatizing reagent shown.
[0055] In the present invention, the F substituent on the benzene ring in the first compound is substituted by the pyrrolyl group in the secon...
Embodiment 1
[0068] Preparation of a fluorine-containing chiral derivatizing reagent (c):
[0069] Dissolve 5.0 mM 2-fluoro-4-nitrobenzaldehyde (2F5NBA) in ethanol and 7.5 mM trans-4-fluoro-L-proline in deionized water, respectively, and mix the two. The substance ratio of 2-fluoro-4-nitrobenzaldehyde (2F5NBA) to trans-4-fluoro-L-proline in the solution was 1:1.5, and 50 mM NaOH was added to adjust the pH of the solution to 10.5. The reaction was carried out at 25 °C for 15 min to obtain a fluorine-containing chiral derivatizing reagent (c). The chemical equation is shown in the appendix. figure 1 The mass spectrum of the product is shown in the appendix image 3 The resulting mass spectral data are as follows:
[0070] ESI-MS: 283.07211, Theory: [M+H] + : 283.06520.
[0071] The yield of the product was calculated to be 94% from the ratio of the integral area of the fluorine spectrum of the starting material to the chiral derivatizing reagent.
Embodiment 2
[0073] Preparation of a fluorine-containing chiral derivatizing reagent (c1):
[0074] The rest are the same as Example 1, the difference is: the raw material "2-fluoro-4-nitrobenzaldehyde (2F5NBA)" is changed to "3-fluoro-5-nitrobenzaldehyde (3F5NBA)", "adding 50 mM NaOH to adjust the pH of the solution to 10.5" was changed to "Add 50 mM NaOH to adjust the pH of the solution to 10" to obtain a fluorine-containing chiral derivatization reagent (c1) with a yield of 95%. The chemical equation is as attached. Figure 4 shown.
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