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I'm not an expert teacher or lecturer of chemistry. I was only a student from SMA NEGERI 15 SURABAYA who had been one of the Bronze Medalist Participants of Olimpiade Sains Nasional X (2011) of Chemistry In Manado, North Sulawesi, 11 - 16 September 2011 and graduated in 2012. Now, I'm studying at Universitas Airlangga in Surabaya, Indonesia. I do love chemistry and I would like to help them who had difficulties in studying chemistry. That's why, please understand me if you found some misconcepts in my entries. Suggestions are always necessary in order to develop this blog. And I'm sorry because my English isn't so well.

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The Documents

Friday, December 30, 2011

Perindopril


(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

Perindopril, or perindopril arginine, (trade names include Coversyl and Aceon) is a long-acting ACE inhibitor. Perindopril is used to treat high blood pressure, heart failure or stable coronary artery disease. It is also available in a generic form, perindopril erbumine. According to the Australian government's Pharmaceutical Benefits Scheme website, based on data provided to the Australian Department of Health and Aging by the manufacturer, perindopril arginine and perindopril erbumine are therapeutically equivalent and may be interchanged without differences in clinical effect. However the dose prescribed to achieve the same effect will differ due to different molecular weights for the two forms.

For Perindopril as treatment for hypertension, the initiation dose is 5 mg perindopril arginine (or 4 mg perindopril erbumine) once daily, then the dose may be increased to 10 mg perindopril arginine (or 8 mg perindopril erbumine) after 1 month of treatment to improve blood pressure control or in case of concomitant stable coronary artery disease.

Synthesis (My Version)
There are 5 chiral atoms in this compound. Because I don't have much knowledge in Stereochemistry, I have to neglect the stereochemistry of this compound.



Substitution reactions are very dominant in my synthesis of this Perindopril. The in situ reaction is needed to protect the amine group with anhydride acetate because I worry that the carboxyl will attact the amine group. The reaction goes in Sn2 reaction so that I need to use HMPA as the solvent. Adding base will remove the protecting group.

The hydroboration to add the Anti-Markovnikov alcohol. The oxidation reaction may be created by adding PCC because the only group that will be affected with PCC is the alcohol. And the last is the Sn1 reaction.

Further Reading . . .
Wikipedia


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