Solid-Phase Preparation of a Library Based on a Phenylalanine Scaffold

• Published in: QSAR & combinatorial science Vol. 24; no. 8; pp. 913 - 922
• Main Authors: Colombo, Aina, Fernàndez, Joan-Carles, de la Figuera, Natalia, Fernández-Forner, Dolors, Forns, Pilar, Albericio, Fernando
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.10.2005; WILEY‐VCH Verlag
• Subjects: 4-Iodophenylalanine; Combinatorial Chemistry; Phenylalanine; Solid-phase; Suzuki
• ISSN: 1611-020X; 1611-0218
• DOI: 10.1002/qsar.200420105

A convenient strategy (preliminary study, preproduction and production) for the solid‐phase preparation of a library using 4‐iodophenylalanine as a scaffold is described. The aromatic ring was first modified via the Suzuki reaction and the amino position was subsequently derivatized into amides, sulfonamides, amines, carbamates and ureas. The scope and limitations of all of the reactions carried out in parallel are discussed. The solid‐phase synthesis of a library of 315 individual compounds was attempted by using seven boronic acids and nine representative compounds from each of the following classes: carboxylic acids, sulfonyl chlorides, aldehydes, alcohols and isocyanates. Owing to the failure of the amine derivatization, 297 compounds were ultimately obtained.