1220710-20-2Relevant academic research and scientific papers
Acetonide protection of dopamine for the synthesis of highly pure N-docosahexaenoyldopamine
Liu, Zhongqiang,Hu, Bi-Huang,Messersmith, Phillip B.
, p. 2403 - 2405 (2010)
Direct acetonide protection of the catechol of dopamine has proven to be problematic due to the formation of Pictet-Spengler isoquinolines. Here we report an efficient method for acetonide protection of dopamine, allowing the preparation of a dopamine prodrug without complications from the Pictet-Spengler reaction. Acetonide-protected dopamine was first synthesized by pre-protecting the amino group with phthaloyl followed by refluxing with 2,2-dimethoxypropane in the presence of TsOH. Further work demonstrated that Fmoc and trifluoroacetyl were also suitable N-protective groups, while Boc-protected dopamine gave an isoquinoline product. Acetonide-protected dopamine was coupled to DHA (all cis-4,7,10,13,16,19-docosahexaenoic acid) to produce the N-DHA-dopamine prodrug with high purity.
Method of synthesizing acetonide-protected catechol-containing compounds and intermediates produced therein
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Page/Page column 26, (2012/07/30)
The inventors disclose here a novel, facile approach to the synthesis of acetonide-protected catechol-containing compounds having at least one amine group. In specific embodiments, the invention provides novel methods of synthesizing 3,4-dihydroxyphenylalanine (H-DOPA(acetonide)-OH (6)), Fmoc-protected H-DOPA(acetonide)-OH (Fmoc-DOPA(acetonide)-OH (7)), Fmoc-protected dopamine (Fmoc-dopamine(acetonide) (10)), TFA-protected dopamine (TFA-dopamine(acetonide) (13)) and acetonide-protected 4-(2-aminoethyl)benzene-1,2-diol (acetonide-protected dopamine (14)).
