Water-soluble derivate of 2,6-diisopropyl phenol and use thereof
A technology of propyl phenol ester and water-soluble compound, which is applied in the direction of sugar derivatives, sugar derivatives, medical preparations containing active ingredients, etc., and can solve problems such as poor stability
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Embodiment 1
[0039] Embodiment 1: the synthesis of compound 4 or 5
[0040] To a solution of phosgene in dichloromethane (10%, 10 mL), under cooling and stirring in ice water, slowly add a solution of 2,6-diisopropylphenol in dichloromethane (1.78 g / 10 mL, 0.01 mol) dropwise. After the addition was complete, continue to stir for 30 minutes, and distill off the solvent under reduced pressure. The residue was dissolved in 10 ml of methylene chloride, and then distilled off the solvent under reduced pressure. The residue was dissolved in 20 ml of anhydrous ethylene glycol dimethyl ether, Under ice water cooling and stirring, slowly drop 20 ml of ethylene glycol dimethyl ether mixed solution of glucosamine hydrochloride and triethylamine (containing 2.16 g of glucosamine hydrochloride and 2.8 ml of triethylamine). The mixture naturally Stir for 1 hour, evaporate the solvent under reduced pressure (heating is less than 30 ° C), the residual solid is washed with dichloromethane to remove impurit...
Embodiment 2
[0041] Embodiment 2: the synthesis of compound 8
[0042] Dissolve triphosgene (2.65g, 0.01mol) in 100ml of anhydrous dichloromethane, slowly add 10ml of 2,6-diisopropylphenol (1.80g, 0.01mol) dropwise at 0°C without Water dichloromethane solution, after the addition, stirred at 5°C for 30 minutes, kept at 0-5°C, glucamine (glucamine 7) (1.8g, 0.01mol) in 5 ml of anhydrous ethylene glycol dimethyl ether solution, After the addition, stir at room temperature for 1 hour, and evaporate the solvent under reduced pressure at less than 30°C. The residue is dissolved in 100 ml of water, filtered to obtain a clear solution, and freeze-dried to obtain compound 8 (3.65g, 95%). The weight loss on drying analysis is Contains 2 crystalline waters. Mass spectrum (ESI) 386.5 (M+1).
Embodiment 3
[0043] Embodiment 3: the synthesis of compound 10
[0044] A dichloromethane solution containing oxalyl chloride (1M, 10ml, 0.01mol) was cooled to 0°C, and 10ml of anhydrous dichloromethane containing 2,6-diisopropylphenol (1.80g, 0.01mol) was slowly added dropwise. Methane solution, continued to stir for 30 minutes, under ice water cooling and stirring, slowly added dropwise 20 ml of ethylene glycol dimethyl ether mixed solution of glucosamine hydrochloride and triethylamine (containing 2.16 grams of glucosamine hydrochloride, three ethylamine 4.5 milliliters). The mixture was naturally stirred for 1 hour, and the solvent was evaporated under reduced pressure (heating was less than 30° C.), the residual solid was washed with dichloromethane to remove impurity salts, and the solid was redissolved in 100 milliliters of water, and freeze-dried to obtain white solid compound 10 (3.71g, 81%). Loss on drying analysis showed 2.5 crystal water. Mass spectrum (ESI) 412.4 (M+1).
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