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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: Abdul Ghani, Aliyin
Format: Thesis
Language:English
Published: 2010
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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spelling my.uitm.ir.1009752024-08-22T17:04:06Z https://ir.uitm.edu.my/id/eprint/100975/ Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani Abdul Ghani, Aliyin 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. 2010 Thesis NonPeerReviewed text en https://ir.uitm.edu.my/id/eprint/100975/1/100975.pdf Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani. (2010) Degree thesis, thesis, Universiti Teknologi MARA (UiTM).
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
language English
description 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.
format Thesis
author Abdul Ghani, Aliyin
spellingShingle Abdul Ghani, Aliyin
Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
author_facet Abdul Ghani, Aliyin
author_sort Abdul Ghani, Aliyin
title Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
title_short Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
title_full Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
title_fullStr Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
title_full_unstemmed Synthesis and decarboxylation of diketoester towards the synthesis of dysidamide C / Aliyin Abdul Ghani
title_sort synthesis and decarboxylation of diketoester towards the synthesis of dysidamide c / aliyin abdul ghani
publishDate 2010
url https://ir.uitm.edu.my/id/eprint/100975/1/100975.pdf
https://ir.uitm.edu.my/id/eprint/100975/
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score 13.211869

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