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12th October 2010 @ 08:53
Determination of the optical rotation of [i]S[/i]-(+)-Praziquanamine in dependency of the [i]ee[/i] See also: [*] [url=http://www.ourexperiment.org/racres_pzq/696] Hydrolysis of [i]S[/i]-(+)-PZQ[/url] [*] [url=http://www.ourexperiment.org/racres_pzq/717]Optical rotation of [i]R[/i]-(-)-PZQ and [i]S[/i]-(+)-PZQ[/url] [data=size:200x150]531[/data] [b][i]S[/i]-(+)-PZQamine:[/b] m.p. 117-118°C (lit.[1] 117-119°). [α]D20 = 296° (c=1, DCM) ([α]D20 for R-(-)-PZQamine: -306° (c=?, solvent=?) [2]) [b]Determination of the optical rotation α in dependence of the [i]ee[/i] (in %)[/b] To a solution of [i]S[/i]-(+)-PZQamine (c = 1, DCM) was added a solution of [i]rac[/i]-PZQamine (c = 1, DCM) (vol/vol) to give a total volume of 1 mL. [data=size:250x150]827[/data] [i]Chart 1: [/i]Optical rotation α as a function of the [i]ee[/i] [data=size:400x250]535[/data] Small deviations due to the volatile solvent DCM. [b]Result:[/b] Linear dependence of the optical rotation α of [i]S[/i]-(+)-PZQamine on the [i]ee[/i] (determined for a concentration c = 1 in DCM) [b]References:[/b] [url=http://dx.doi.org/10.1016/S0040-4020(98)00401-3][1] “Formation of Pyrazinoisoquinoline Ring System by the Tandem Amidoalkylation and N-Acyliminium Ion Cyclization: An Efficient Synthesis of Praziquantel”, J. H. Kim, Y. S. Lee, H. Park and C. S. Rim, Tetrahedron 1998, 54, 7395-7400.(DOI: doi:10.1016/S0040-4020(98)00401-3)[/url] [url=http://v3.espacenet.com/publicationDetails/biblio?DB=EPODOC&adjacent=true&locale=en_ep&FT=D&date=19750123&CC=DE&NR=2331713A1&KC=A1][2] “Pyrazinoisochinolin-Derivat“, R. Polke, F. Loebich, J. Seubert, H. Thomas and P. Andrews, German Patent Application (1975) DE 2,331,713.[/url]
Attached Files
Scheme
Table1
Chart Dependency optical rotation - ee
Chart Dependency optical rotation - ee new.jpg