Continuous preparation process of 2 '-O-methyl-2-amino adenosine
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An aminoadenosine and preparation process technology, applied in the preparation of sugar derivatives, sugar derivatives, organic chemistry, etc., can solve the problems of low yield and complicated purification, achieve process safety, simplify post-processing purification steps, reduce The effect of chemical reagents
Inactive Publication Date: 2022-06-17
凯泽合成科技(常熟)有限公司
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Problems solved by technology
Especially the synthesis of 2'-O-methylguanosine is challenging
Through literature research, 2-aminoadenosine was directly methylated by methylating reagents such as methyl iodide or dimethyl sulfate, but the existence of 3'-O-methyl isomers made the purification complicated. usually low yield
And if you want to avoid the 3'-O-methyl isomer, you need to use expensive 1,3 dichloro-1,1,3,3-tetraisopropyldisiloxane reagent, the route needs at least two more step
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[0019] like figure 2 As shown, the continuous preparation process of 2'-O-methyl-2-aminoadenosine, the steps include:
[0020] (1) Dissolve 282.3 g of 2-aminoadenosine in 1411 ml of N,N-dimethylformamide, add 11.3 g (0.05 equivalent) of stannous chloride dihydrate to prepare a homogeneous solution; 0.2 mol of diazonium Methane was dissolved in 15L tetrahydrofuran solution, wherein diazomethane was prepared as needed and prepared as needed;
[0021] (2) Automatic feeding, 2-aminoadenosine is fed from pump A at a rate of L=5.6g / min, and diazomethane is fed from pump B at a rate of L=24.0g / min, entering the coil reaction The reaction is carried out in the reactor, the temperature of the coil reactor is controlled at 60-70 ° C in the water bath, the retention time is 20 minutes, the reaction product is received at the discharge port, the activated carbon is decolorized, and after concentration, the product 2'-O-methyl-2-amino acid is obtained by crystallization. glycoside, whit...
[0025] Solution B: diazomethane tetrahydrofuran solution (0.2mol / L), feed rate L=3g / min, and the molar ratio of 2-aminoadenosine to diazomethane is controlled at about 1:1.25;
[0026] (3) Reaction conditions: use a coiled tube reactor, external bath at 60-70°C, retention volume: 100ml, retention time RT=21min, post-treatment to obtain 9.0g of product with a yield of 91% and a purity of 99%.
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Abstract
The invention provides a continuous preparation process of 2 '-O-methyl-2-amino adenosine, which comprises the following steps: (1) dissolving a substrate 2-amino adenosine and a catalyst Lewis acid in a first solvent to obtain a solution A, and dissolving a methylation reagent diazomethane in a second solvent to obtain a solution B; (2) enabling the solution A to enter a reactor through a pump A at a certain feeding speed, enabling the solution B to enter the reactor through a pump B at a certain feeding speed, adjusting the feeding speed so that the molar ratio of 2-amino adenosine to diazomethane is basically controlled to be 1: (1-1.25), controlling the temperature in the reactor to be 20-100 DEG C and the retention time of a reaction system in the reactor to be 15-30 minutes, receiving a reaction product through a discharge port, and obtaining the 2-amino adenosine diazomethane. And concentrating and crystallizing to obtain a 2 '-O-methyl-2-amino adenosine solid. By adopting a continuous diazomethane methylation method, continuous industrial production can be realized, the production time is greatly shortened, and the process is safe, stable and efficient.
Description
technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a continuous preparation process of 2'-O-methyl-2-aminoadenosine. Background technique [0002] 2'-O-methyl ribonucleosides are widely distributed in RNA and have been the focus of extensive synthetic work since the late 1950s. Especially the synthesis of 2'-O-methylguanosine is challenging. Through literature research, 2-aminoadenosine was directly methylated by methylation reagents such as methyl iodide or dimethyl sulfate, but the existence of 3'-O-methyl isomer complicates purification, Usually the yield is very low. If the 3'-O-methyl isomer is to be avoided, the expensive 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane reagent needs to be used, and the route needs at least two more step. With the rise of small nucleic acid drugs and the increasing demand for raw materials, the development of cost-effective 2'-O-methylguanosine synthesis methods has become more and more i...
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