Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
In this research, glycine methyl ester which was used as a starting material was reacted with methyl malonate potassium salt with the presence of dicyclohexylcarbodiimide (DCCI) via condensation reaction. The product was tested on a TLC plate where several spots were observed indicating major produc...
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| Main Author: | |
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| Format: | Thesis |
| Language: | English |
| Published: |
2010
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| Online Access: | https://ir.uitm.edu.my/id/eprint/100975/1/100975.pdf https://ir.uitm.edu.my/id/eprint/100975/ |
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| Summary: | In this research, glycine methyl ester which was used as a starting material was reacted with methyl malonate potassium salt with the presence of dicyclohexylcarbodiimide (DCCI) via condensation reaction. The product was tested on a TLC plate where several spots were observed indicating major products, some unreacted materials and impurities, therefore the synthesized compound was purified via recrystallization technique. The product was cyclized by reacting it with sodium methoxide, produce by reaction between sodium metal and anhydrous methanol generated in situ, which acts as a base and abstracts the acidic proton bonded to the carbon in between the carbonyl groups forming an enolate ion via Dieckmann cyclization. The cyclized product undergo decarboxylation reaction by reacting it with acetonitrile and the methyl ester group at C3 position on the pyrrolidinone ring was cleaved, thus removal of carbon dioxide. All the synthesized compounds were characterized by using spectroscopie techniques such as *H NMR, 13C NMR and FTIR. |
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