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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.
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.

Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine

  • Received Date: 2010-05-02
  • Rev Recd Date: 2010-05-27
  • 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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    沈阳化工大学材料科学与工程学院 沈阳 110142

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Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine

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.

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.
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.

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