发明名称 |
Process for the preparation of derivatives of 4-amino-3-hydroxypyrrole-2-carboxylic acid |
摘要 |
Novel processes and intermediates are provided for the synthesis of derivatives of 4-amino-3-hydroxypyrrole-2-carboxylic acids that are useful as monomers for polyamides capable of binding dsDNA. According to one preferred reaction scheme, an alkyl alkoxymethylene nitroacetate (Formula VIII) is prepared by reaction of a trialkyl orthoformate or orthoacetate with a nitroacetate ester in the presence of a carboxylic anhydride. The compound of Formula VIII is condensed with an N-substituted glycine to yield an N-substituted (2-nitro-2-alkoxycarbonyl)vinyl glycinate ester (Formula VII). Ring closure in the presence of an alkali metal alkoxide yields a 4-nitro-3-hydroxypyrrole-2-carboxylic ester (Formula V). After blocking of the 3-hydroxy group to produce a further intermediate (Formula IV), the 4-nitro group is reduced to a 4-amino group (Formula III), and the 4-amino group is then blocked by reaction with a dicarbonate diester to produce the fully blocked intermediate (Formula II). Saponification of the 2-carboxylic acid ester yields a monomer having a free 2-carboxylic ester moiety (Formula I).
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申请公布号 |
US2004014984(A1) |
申请公布日期 |
2004.01.22 |
申请号 |
US20030332181 |
申请日期 |
2003.05.09 |
申请人 |
PHILLION DENNIS P;SINGH MEGH |
发明人 |
PHILLION DENNIS P;SINGH MEGH |
分类号 |
C07C229/30;C07D207/36;C07D207/42;(IPC1-7):C07D207/28;C07F7/02 |
主分类号 |
C07C229/30 |
代理机构 |
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