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KMID : 0370220030470050276
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Yakhak Hoeji
2003 Volume.47 No. 5 p.276 ~ p.282
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Synthesis of N-Aryl Phenylglycine O-Alkyl Esters and Its Substitution of Ester Moiety
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박명숙/Park MS
박해선/Park HS
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Abstract
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For the development of new synthesis method for unnatural amino acid esters. N- aryl phenylglycine O-alkyl esters 4a~I were synthesized through esterification, br omination, 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 3 h 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.
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KEYWORD
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