A Facile and Efficient Multi‐Gram Synthesis of  N ‐Protected 5‐(Guanidinocarbonyl)‐1 H ‐pyrrole‐2‐carboxylic Acids | Zendy

Schmuck Carsten | Zendy; Bickert Volker | Zendy; Merschky Michael | Zendy; Geiger Lars | Zendy; Rupprecht Daniel | Zendy; Dudaczek Jürgen | Zendy; Wich Peter | Zendy; Rehm Thomas | Zendy; Machon Uwe | Zendy

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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)

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