"Synthese von IMIDs®"
Synthese von den immunmodulatorischen Substanzen Revlimid, Actimid und Thalidomid
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The purpose of this diploma thesis was the synthesis of three different IMIDs Thalidomid, Revlimid and Actimid. The representation of Thalidomid occurered by three different ways and the conversion of isobenzfuran-1,3-dione and 2,6-dioxopiperidin-3-aminium bromide brought the best yield in DMF and triethylamine. Two other synthesis ways could be carried out which also led to the end product Thalidomid, but in doing so, the yield was lower. Once the open-chained glutamine acid was, in first step, converted with the isobenzfuran-1,3-dione to the glutamine acid derivate and afterwards the ring en...
The purpose of this diploma thesis was the synthesis of three different IMIDs Thalidomid, Revlimid and Actimid. The representation of Thalidomid occurered by three different ways and the conversion of isobenzfuran-1,3-dione and 2,6-dioxopiperidin-3-aminium bromide brought the best yield in DMF and triethylamine. Two other synthesis ways could be carried out which also led to the end product Thalidomid, but in doing so, the yield was lower. Once the open-chained glutamine acid was, in first step, converted with the isobenzfuran-1,3-dione to the glutamine acid derivate and afterwards the ring end carried out by the 2,6-dioxotetrahydro- 2H-pyran derivate and the glutamine derivate. In the third synthesis way both source materials from the first reaction guidance were heated up with formic acid under backflow. Likewise, to synthesis the IMID Revlimid several reaction guidance were carried out. The synthesis way with the highest yield proceeded via the alkylation with following ring end to the Amid with 2,6-dioxopiperidin-3-aminium bromide and methyl 2-(bromomethyl)-3- nitrobenzoate.
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