Paper
Synthesis,Spectrum Characterization and Crystal Structure of (4S,5S)-4,5-dicarboxamide-2-(2-bromophenyl)-1,3-dioxolane
Published 2010 · Song Jun-song
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Abstract
(4S,5S)-4,5-dicarboxamide-2-(2-bromophenyl)-1,3-dioxolane is the key intermediate which can be synthesized for anticancer drugs.The title compound was synthesized from 2-bromobenzaldehyde and D-ethyl tartrate as starting materials,which can be prepared by the condensation reaction and ammonolyzed by ammonia.The effects of ratio of substances,amount of catalyst and reaction time on yield were discussed.The most favorite technological conditions of title compound(Ⅰ) were determined as follows:n(D-ethyl tartrate)∶n(2-bromobenzaldehyde)=1.3∶1,catalyst dosage=4.5% of mass of the reactants,cyclohexane 10 mL,reaction time 6 h;pumped ammonia 4 h at room temperature,recrystallized from ethanol to obtain final product,the yield was 67.1%,m.p.113～114 ℃.The single crystal was obtained by dissolving product in ethanol and evaporating at room temperature.The structure of the product was characterized by melting point,elementary analysis,MS,1HNMR and X-ray single crystal diffraction.The crystal belongs to monoclinic system with space group P21 and crystallographic data of the compound are:a=94.150(19) nm,b=144.58(3)nm,c=96.170(19) nm,α=90.00°,β=111.14(3)°,γ=90.00°,V=1.2210(5)nm3,Dx=1.714 g/cm3,Z=4,F(000)=632,μ=3.38 mm-1,S=1.00,R=0.063,wR=0.181.
The synthesized compound (4S,5S)-4,5-dicarboxamide-2-(2-bromophenyl)-1,3-dioxolane) shows promising potential as an anticancer drug intermediate, with a yield of 67.1% and crystallographic data in the monoclinic
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