Solid-phase synthesis of trisubstituted 2-imidazolidones and 2-imidazolidinethiones

Journal of Combinatorial Chemistry

Volumn 1, Issue 3, 1999, Pages 195-198

  Nefzi, Adel ^a   Ostresh, John M ^a   Giulianotti, Marc ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001758406     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc980019m     Document Type: Article

References (30)

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17. The N-alkylated MBHA resin could be cleaved with 70% TFA in DCM in 30 min.
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22. The products were run on a Vydac Cis column, using a 5-95% gradient of 0.05% TFA in ACN in 7 min. The purity was estimated using analytical traces at 214 nm. The yields obtained in all cases were higher then 75% relative to the initial loading of the resin.
23. 2 included also β-Ala (leading to the six-member rings of cyclic ureas and cyclic thioureas) and the D- and L- forms of Glu(tBu).
24. Functionalized amino acids such as Lys, Gin, and Asn were excluded in the second position. Following the reduction of the amide bonds, the generated secondary amine (resulting from the side chain of Lys) or primary amines (resulting from the side chains of Gin and Asn) compete during the cyclization step with the two other secondary amines, leading to the generation of multiple compounds.
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