N-叔丁氧羰基-DL-(±)-高酪氨酸的合成
Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine
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摘要: 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。
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关键词:
- N-叔丁氧羰基-DL-(±)-高酪氨酸 /
- 合成 /
- L-天冬氨酸 /
- Friedel-Crafts反应 /
- 催化氢化
Abstract: Objective To prepare N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine(1),a key unusual amino acid and pharmaceutical intermediate for the total synthesis of novel peptides drug including cyclic or straight chain peptide. Methods Starting from L-aspartic acid(2),the target compound 1 was synthesized via 6 steps including N-methoxycarbonylation,intramolecular dehydration and anhydridation,Friedel-Crafts reaction with 2-chloroanisole,catalytic hydrogenation with 10% Pd-C,N-demethoxycarbonylation and demethylation with 48% HBr-HOAc followed by N-Butoxycarbonylation. Results Target compound 1 had been successfully synthesized in an overall yield of 49.7%.The structure of the target compound was confirmed by ESI-MS,1H NMR and 1C NMR. Conclusion The process developed has several advantages such as cheap materials,convenient workup and high yield. -
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