Isoserine ester derivant and method of preparing the same
A technology of isoserine ester and phenylisoserine methyl ester, which is applied in the field of chemical synthesis and pharmaceuticals, and can solve the problems of many operation steps, low yield of P condensation of taxane parent core, and difficult separation.
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Embodiment 1
[0146] Embodiment 1: Preparation of 3-phenylisoserine methyl ester hydrochloride
[0147]Dissolve 50g of 3-hydroxy-4-phenylazetidin-2-one (HPA) in 300ml of methanol, pass HCl gas into the methanol solution of HPA under stirring condition, and after 3-4 hours, dissolve it with ethyl acetate The ester was used as a developer for TLC detection, and the test results showed that the raw materials disappeared, and then the reaction solution was concentrated under reduced pressure to a dry syrupy product (60 g, 100%), which was directly used in the next reaction.
[0148] 1 H NMR (DMSO, 500MHz): δ8.77(s, 1H), δ7.50(t, 2H), δ7.41(m, 3H), δ6.85(bs, 1H), δ4.49(d, 1H), δ4.36(s, 1H), δ3.47(s, 3H). MS(m / z): 196(M+1)
Embodiment 2
[0149] Embodiment 2: Preparation of N-benzoyl-3-phenylisoserine methyl ester
[0150] 3-Phenylisoserine methyl ester hydrochloride (all obtained in Example 1) was dissolved in 1000ml CH 2 Cl 2 and 100ml of triethylamine (TEA), then add 66ml of TEA, cool down to -5°C, start to drop 22.6ml of benzoyl chloride in dichloromethane (200ml) solution (about 30 minutes), after the dropwise addition The reaction was stirred for 2 hours, and TLC (ethyl acetate / n-hexane=2 / 1, v / v) showed that the reaction was complete.
[0151] After the reaction is complete, pour the reaction solution into a 3L beaker, wash the reaction bottle with 500ml of dichloromethane, put it into the beaker, add 500ml of pure water, stir fully, separate the liquids, back-extract the aqueous phase with 250ml of dichloromethane, combine the organic phases, and The phase was washed with 700ml of 1N hydrochloric acid and separated, and the organic phase was washed with saturated sodium chloride solution 1 (500ml), sep...
Embodiment 3
[0154] Example 3: Preparation of N-benzoyl-2-oxo-tert-butoxycarbonyl-3-phenylisoserine methyl ester
[0155] Dissolve 30g of N-benzoyl-3-phenylisoserine methyl ester in 250ml of dichloromethane, then add 1.23g of dimethylaminopyridine and 18ml of triethylamine, stir for 5 minutes, and start to drop at about 10°C Add 26.25g of di-tert-butyl dicarbonate in dichloromethane (100ml) solution (about 20 minutes), continue to stir and react for 20 minutes after the dropwise addition is complete, TLC (ethyl acetate / n-hexane=2 / 1, v / v) Shows complete reaction.
[0156] After the reaction is completed, add 200ml of pure water to wash, separate the layers, wash the organic phase with 5.7% sodium dihydrogen phosphate (200ml×2), and then wash with half-saturated NaCl (200ml, a solution made of saturated saline and water 1 / 1) Wash with saturated NaCl (250ml), dry over anhydrous sodium sulfate, and concentrate to dryness to obtain syrup (40g, 100%).
[0157] 1H NMR (DMSO, 500MHz): δ9.15(s, 1...
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