A kind of preparation method of emtricitabine
A technology of emtricitabine and reaction time, applied in organic chemistry methods, organic chemistry, etc., can solve the problems of low total yield, expensive raw materials and reagents, high cost, etc., and achieve high atom utilization, green reagents, The effect of mild reaction conditions
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Embodiment 1
[0047] Preparation of (1R,2S,5R)-2-isopropyl-5-R-methyl-1-cyclohexyl chloroformate 3:
[0048] Add 15.60g (0.1mol) L-menthol and 156ml dichloromethane to a round-bottomed three-necked flask equipped with mechanical stirring, a thermometer, a constant-pressure feeding funnel and an exhaust gas absorption device, stir to fully dissolve, and cool to -5°C , add 14.84g (0.05mol) triphosgene and continue stirring to make it fully dissolved, then dropwise add a solution of 37.44g triethylamine and 78ml dichloromethane, and the dropwise addition is completed in about 1.5 hours. Incubate the reaction for 2 hours, enter the second reaction stage, be warming up to 25 ° C, and stir the reaction for about 6 hours. After the reaction is completed, the precipitate is separated by filtration. Washed with brine, dried with anhydrous sodium sulfate, and finally rectified under reduced pressure to collect 95-96°C, 5 mmHg fractions to obtain 19.73 g of colorless oily compound 2, with a yield of 9...
Embodiment 2
[0050] Preparation of but-2-ene-1,4-diylbis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)bis(carbonate)4:
[0051] In a round-bottomed three-necked flask equipped with a mechanical stirring, a thermometer, and a constant-pressure feeding funnel, add 4.93g (0.052mol) butenediol, 30ml dichloromethane, stir well, cool to 0°C in an ice-water bath, add 6.48g triethyl ether amine, stir evenly, dissolve the obtained 21.88g (0.10mol) of compound 2 in 45ml of dichloromethane and slowly add it dropwise to the three-necked flask, stir and react for 1 hour, separate out the precipitate by filtration, and wash the mother liquor with saturated sodium bicarbonate solution, It was then dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain 18.98 g of compound 4 with a yield of 84%. 1 H-NMR (CDCl 3 )δ: 5.88(t, 2H), 4.77(d, 4H), 4.51(m, 2H), 1.83(m, 2H), 1.75-1.50(t, 4H), 1.63-1.38(m, 8H), 1.54 (m, 2H), 1.41 (m, 2H), 0.86 (d, 6H), 0.83 (d, 12H). Elemental Analysis C 26 O...
Embodiment 3
[0053] Preparation of (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl(2-oxoethyl)carbonate:
[0054] Add 2.52g (0.01mol) tungstic acid, 17.41ml (0.30mol) 50% H to a round-bottomed three-necked flask equipped with mechanical stirring and a thermometer in turn 2 0 2 Aqueous solution, 83ml of n-butanol solution, stirred for half an hour, then added 22.59g (0.05mol) of compound (4) obtained, stirred evenly, heated to 80°C, reacted for 5 hours, removed the catalyst by centrifugation, extracted, and the organic phase was dried with anhydrous After drying over magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 18.83 g of compound 5 in a yield of 79%. 1 H-NMR (CDCl 3 ) δ: 9.65(s, 2H), 4.67(s, 2H), 4.51(m, 1H), 2.10(m, 1H), 2.00(m, 1H), 1,70(m, 2H), 1.51(m , 2H), 1.28 (m, 1H), 1.12 (m, 2H), 0.9 (m, 6H), 0.81 (d, 3H). Elemental Analysis C 13 H 22 O 4 Measured value (%): C65.48, H9.15, 026.40; Theoretical value (%) C64.44, H9.15, O26.41.
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