A kind of method for preparing tyrosine-o-sulfonate
A technology of tyrosine and sulfonate, which is applied in the field of medicine, can solve the problems of complex purification methods of reaction products and restrictions on large-scale production of products, and achieve the effect of avoiding column chromatography purification operations, improving purity, and simple operation
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[0024] The method for preparing tyrosine-O-sulfonate of the present invention comprises the steps:
[0025] (1) In the presence of diluent and alkali, the tyrosine of sulfonation reagent and Fmoc protection is reacted, obtains reaction solution;
[0026] (2) the reaction solution of step (1) is poured in the poor solvent, then leave standstill;
[0027] (3) decanting the supernatant of the step (2) resultant, dissolving the residue in water, then adjusting the pH to weak acidity with alkali;
[0028] (4) washing the aqueous solution obtained in step (3) with a good solvent, and then concentrating;
[0029] (5) Add a good solvent to the concentrate in step (4) and stir, filter, add the filtrate to the poor solvent, stir, collect the solid, dry to obtain a solid;
[0030] Wherein, Fmoc is 9-fluorenylmethoxycarbonyl, which is connected with amino group.
[0031] In this specification, unless otherwise stated, the operations are all carried out at normal temperature and pressur...
Embodiment 1
[0058] Add 32.4 grams of Fmoc-L-tyrosine to the reaction flask, then mix 200 milliliters of N,N-dimethylformamide, 50 milliliters of pyridine and 25 milliliters of 1,4-dioxane into Stir to dissolve in the reaction flask, weigh 12.4 g of the DMF sulfur trioxide compound and add it to the reaction flask, and start stirring overnight at room temperature. TLC followed the reaction until the reaction of Fmoc-L-tyrosine was complete.
[0059] The reaction solution was poured into 1200 ml of frozen diethyl ether, and the resulting mixed solution was left overnight at -20°C. The supernatant was decanted, and the residual oil was dissolved in 250 ml of ice water, and then adjusted to pH 6.5 with 10% aqueous sodium hydroxide solution. During the process, the temperature of the system was kept below 0° C., and the resulting solution was lyophilized. Add 250 ml of methanol to the resulting lyophilized solid and stir for 30 minutes, filter, add the filtrate to 2.5 liters of frozen ether, ...
Embodiment 2
[0063] Add 32.4 grams of Fmoc-L-tyrosine to the reaction flask, then mix 200 milliliters of N,N-dimethylformamide, 50 milliliters of pyridine and 25 milliliters of 1,4-dioxane into Stir to dissolve in the reaction flask, weigh 12.4 g of sulfur trioxide N,N-dimethylformamide complex, add it into the reaction flask, and start stirring at room temperature. TLC followed the reaction until the reaction of Fmoc-L-tyrosine was complete.
[0064] The reaction solution was poured into 1200 ml of frozen diethyl ether, and the resulting mixed solution was left overnight at -20°C. The supernatant was decanted, and the residual oily matter was dissolved in 250 ml of ice water, adjusted to pH 6.5 with 10% NaOH aqueous solution, and the temperature of the system was kept below 0°C during the process. The resulting aqueous solution was washed with ethyl acetate (150 ml*3), and then rotary evaporated to dryness at 35°C. Add 250 milliliters of methanol and stir for 30 minutes, filter, add the...
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