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Synlett 2005(3): 496-500  
DOI: 10.1055/s-2005-862371
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Short and Efficient Protocol for the Solid-Phase Synthesis of Retro-Inverso Surrogates

Markus M. Vögtle, Andreas L. Marzinzik*
Novartis Institutes for BioMedical Research, WSJ-507, 4002 Basel, Switzerland
Fax: +41(6132)46589; e-Mail: andreas.marzinzik@pharma.novartis.com;
Further Information

Publication History

Received 19 November 2004
Publication Date:
04 February 2005 (online)

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Abstract

A novel and straightforward synthesis of malondiamides on solid-phase has been developed. These compounds, which are obtained in good yield and excellent purity, can be used for the synthesis of large lead-finding split-and-mix-libraries.

Key words

combinatorial chemistry - solid-phase synthesis - amides - acylations - peptides

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10

The purity was determined by HPLC at 254 nm and 214 nm and 1H NMR.

11

Under the same conditions up to 90% cross-linking was found when phthaloyldichloride, isophthaloyldichloride or terephthaloyldichloride were used as diacidchlorides.

12

The results of more complex and non-symmetric acid and acid chlorides will be reported in due course.

13

The ratio was determined by HPLC at 254 nm and 214 nm and 1H NMR.

14

The investigation of mono Boc-protected diamines as reactant and their subsequent deprotection on solid-phase is underway in our laboratories and will be reported in due course.