Starting from a chlorotrityl resin-linked hydroxylamine, a hydroxamic dipeptide having serine at the N-terminus was prepd. by using DMTMM [4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride] as the coupling agent. Under microwave heating, Mitsunobu cyclization of the hydroxamic dipeptide gave a 3,6-disubstituted-perhydro-diazepin-2,5-dione in very good yields. Thus, by using Fmoc-Ser-Glu(OCH2CH:CH2)-NH-O-Resin, H3CCO-Gly-OH and H-Pro-OMe, peptidomimetic I was prepd. in four steps in 75% yield.
Solid-Phase Synthesis of Conformationally Constrained Peptidomimetics Based on a 3,6-Disubstituted-1,4-diazepan-2,5-dione Core
RODRIQUEZ, Manuela;
2003-01-01
Abstract
Starting from a chlorotrityl resin-linked hydroxylamine, a hydroxamic dipeptide having serine at the N-terminus was prepd. by using DMTMM [4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride] as the coupling agent. Under microwave heating, Mitsunobu cyclization of the hydroxamic dipeptide gave a 3,6-disubstituted-perhydro-diazepin-2,5-dione in very good yields. Thus, by using Fmoc-Ser-Glu(OCH2CH:CH2)-NH-O-Resin, H3CCO-Gly-OH and H-Pro-OMe, peptidomimetic I was prepd. in four steps in 75% yield.File in questo prodotto:
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