Process for preparation of sulfated derivative of 3,5-diiodo-o-[3-iodophenyl]-l-tyrosine
A sulfation and compound technology, applied in chemical instruments and methods, sulfonic acid preparation, biological testing, etc., can solve problems such as extremely large volume and not necessarily recovery
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preparation example Construction
[0096] T2 is preferably prepared as described.
[0097] The addition of the iodinating agent is carried out at preferably below 25°C in the presence of an aqueous solvent, preferably water.
[0098] Preferably, the iodinating agent is present in a molar ratio of 0.9 to 1.1 mol / mol of compound III (T2).
[0099] After iodination, T3 is isolated as the sodium salt, preferably by filtration, and then converted to the acid form by resuspension in water and acidification with acid, preferably acetic acid or sulfuric acid.
[0100] The acid form is preferably isolated by filtration, resuspended in water to remove salts and filtered.
[0101] T3 as a wet solid was suspended in N,N-dimethylacetamide, the suspension was dehydrated and subjected to sulfation.
[0102] According to a preferred variant, the molar ratio between CSA and T3 is greater than 4, preferably from 4.5 to 10, even more preferably from 7 to 9. Even more preferably, 7.5 to 8.5 mol of CSA / mol of T3. The concentrat...
Embodiment 1
[0141] Example 1. In DMAC T 3 Preparation of S
[0142] The total amount of raw materials is expressed relative to 100 g of T3.
[0143] Under nitrogen atmosphere, 3,5-diiodo-O-(4-hydroxy-3-iodophenyl)-L-tyrosine (100 g; 0.154 mol) was suspended in DMAC (2.0 L) and stirred vigorously to avoid precipitation of solids. After cooling to -5°C, CSA (142.2 g; 1.229 mol) was added dropwise within 40 minutes while maintaining the temperature between -5 and 5°C. At the end of the addition, cooling was stopped and the reaction mixture was left under stirring for about 4 h. The reaction mixture was added dropwise to a stirred aqueous solution of sodium bicarbonate (335.5 g; 3.994 mol aqueous solution, 4.5 L) over 1.5 h. At the end of the addition, a crystalline solid precipitate was observed over time from the solution thus obtained as a mixture of inorganic salts. Filter out this solid, then in Amberlite TM XAD TM 1600, the resulting solution was purified by elution with water / a...
Embodiment 2
[0144] Example 2. Preparation of T from T2 (Levoditi) 3 S
[0145] The schematic diagram of the reaction is as follows:
[0146]
[0147] All raw material quantities are expressed for 1 kg of Levoditi.
[0148] Iodine (about 0.48 kg, source: SQM), NaI (about 0.65 kg, source: Ajay-SQM) and water were charged into the reactor at 18-22°C and stirred until completely dissolved. The resulting iodinated mixture was continuously stirred at room temperature until use.
[0149] Levoditi obtained from L-tyrosine according to the method described in Chalmers, J.R. et al. A. J. Chem. Soc. 1949, 3424-3433), NaI (approx. 0.32 kg) and water were charged to another reactor, And 70% monoethylamine was added.
[0150] The iodination mixture was added to the reaction mixture.
[0151] The resulting suspension was stirred at 18-22 °C for at least 6 h, then cooled to 0 °C within 1 h, stirred for 3-4 h and filtered. The filter cake was washed with water.
[0152] The wet solid was suspend...
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