Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine
- Received Date: 2010-05-02
- Rev Recd Date: 2010-05-27
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Key words:
- N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine /
- synthesis /
- L-aspartic acid /
- Friedel-Crafts reaction /
- catalytic hydrogenation
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.
Citation: | LIU Hong-ming, QIN Ye, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine[J]. Journal of Pharmaceutical Practice and Service, 2010, 28(5): 345-347,384. |