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A Facile and Efficient Multi‐Gram Synthesis of N ‐Protected 5‐(Guanidinocarbonyl)‐1 H ‐pyrrole‐2‐carboxylic Acids
Author(s) -
Schmuck Carsten,
Bickert Volker,
Merschky Michael,
Geiger Lars,
Rupprecht Daniel,
Dudaczek Jürgen,
Wich Peter,
Rehm Thomas,
Machon Uwe
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700756
Subject(s) - chemistry , pyrrole , carboxylic acid , supramolecular chemistry , amide , gram , combinatorial chemistry , ion , decomposition , molecule , organic chemistry , stereochemistry , bacteria , biology , genetics
The synthesis of two versatile building blocks for supramolecular anion binding motifs, 5‐( N ‐Boc‐guanidinocarbonyl)‐1 H ‐pyrrole‐2‐carboxylic acid ( 1 ) and 5‐( N ‐Cbz‐guanidinocarbonyl)‐1 H ‐pyrrole‐2‐carboxylic acid ( 2 ) is reported. Using these building blocks, a guanidiniocarbonyl‐pyrrole anion binding site can easily be introduced into more complex molecules by using standard amide coupling conditions. Both syntheses can be performed on a multi‐gram scale. The products are obtained in pure form and can be stored as solids without decomposition. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)