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(2R,3S)N苯甲酰基3苯基异丝氨酸,是抗癌新药紫杉醇的侧链。利用苯甲醛和氯乙酸乙酯为原料,在甲醇钠作用下,0℃经Darzen反应24h,蒸去甲醇,乙醚萃取,减压蒸馏得到反式3苯基缩水甘油酸乙酯(4),4的甲醇溶液与NH3在100℃中压下氨解,在V(CH2Cl2)/V(CH3OH)=1∶1溶剂中结晶得赤式3苯基异丝氨酰胺(5),5在100℃用Ba(OH)2水解8h,得到赤式3苯基异丝氨酸(6),6与苯甲酰氯于0℃下在w(NaHCO3)=10%的溶液中发生酰化反应,V(THF)/V(CH2Cl2)=4∶1溶剂萃取,粗产物在V(石油醚)/V(丙酮)=40∶1溶剂中结晶,得到赤式N苯甲酰基3苯基异丝氨酸,四步反应总产率为28.4%。用IR、1HNMR、元素分析验证了化合物的结构。
(2R, 3S) N benzoyl 3 phenyl isoserine, is a side chain of anticancer drug paclitaxel. Using benzaldehyde and ethyl chloroacetate as raw materials, under the action of sodium methoxide, Darzen reaction is carried out at 0 DEG C for 24 hours, the methanol is distilled off and the ether is extracted and distilled under reduced pressure to obtain trans-3-phenylglycidyl ethyl ester (4) , 4 methanol solution and NH3 at 100 ° C under pressure ammonia solution, in the V (CH2Cl2) / V (CH3OH) = 1: 1 solvent crystallization was erythro 3 phenylisoserine amide (5), 5 Hydrolysis of Ba (OH) 2 at 100 ℃ for 8h gave erythro-3-phenylisoserine (6). 6 Acylation reaction between benzoyl chloride and benzoyl chloride at 0 ℃ in w (NaHCO3) = 10% , V (THF) / V (CH2Cl2) = 4: 1, the crude product was crystallized from V (petroleum ether) / V (acetone) = 40: 1 solvent to obtain erythro Nbenzoyl 3 Phenylisoserine, the overall yield of the four-step reaction was 28.4%. The structure of the compound was confirmed by IR, 1HNMR, elemental analysis.