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目的制备用于新型多肽类药物全合成研究的非必需氨基酸N-叔丁氧羰基-DL-(±)-高酪氨酸(1)。方法以L-天冬氨酸(2)为原料,经N-甲氧羰基保护、分子内脱水酸酐化、与邻氯苯甲醚的Friedel-Crafts反应、10%钯碳催化氢化、48%氢溴酸脱N-甲氧羰基和酚甲醚保护、N-叔丁氧羰基保护6步反应合成了目标化合物。结果以总收率49.7%成功地合成了目标化合物1,其结构经电喷雾质谱(ESI-MS)、氢谱(1H NMR)和碳谱(13C NMR)确认。结论该合成路线具有原料价廉易得、操作简便、总收率高等优点。
OBJECTIVE To prepare N-tert-butoxycarbonyl-DL- (±) -homotyrosine (1), which is a non-essential amino acid used in the study of the new type of peptide drugs. Methods L-aspartic acid (2) was used as raw material and protected by N-methoxycarbonyl, intramolecular dehydration, Friedel-Crafts reaction with o-chloroanisole, catalytic hydrogenation with 10% palladium on carbon, Bromo-N-methoxycarbonyl and phenol methyl ether protection, N-tert-butyloxycarbonyl protection of 6-step synthesis of the target compound. Results The target compound 1 was successfully synthesized with a total yield of 49.7%. Its structure was confirmed by ESI-MS, 1H NMR and 13C NMR. Conclusion The synthetic route has the advantages of cheap raw materials, easy operation, high total yield.