YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of N-Aryl Phenylglycine Ο-Alkyl Esters and Its Substitution of Ester Moiety

N-Aryl Phenylglycine Ο-Alkyl Esters의 간편한 합성 및 에스테르 치환반응

  • 박명숙 (덕성여자대학교 약학대학) ;
  • 박해선 (덕성여자대학교 약학대학)
  • Published : 2003.10.01
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Abstract

For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through esterification, bromination, C-N bond formation from commercially available phenylacetic acids. An efficient and practical reaction condition for esters 2a∼c was that the starting materials 1a∼c were refluxed in absolute methanol for 3 hours with catalytic concentrated hydrosulfuric acid. In addition, bromines 3a∼c were formated for 3h in dichloromethane at rt with N-bromosuccinimide. Bromines 3a∼c were also converted to 4a∼i through substitution of arylamines during refluxing for 24 hours in ethanol with triethylamine. Interestingly, ethyl esters 5a∼c were formed via transesterification reaction when the p-sulfamylanilino group was used as a nucleophile in ethanol solvent.

Keywords

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