Convert Benzene to Sildenafil Citrate?
See also: cialis |
Convert Benzene to Sildenafil Citrate?
Question:
As a bonus for my Organic Class, I am looking for a detailed mechanism for the synthesis of Benzene to Sildenafil Citrate (Viagra) or the synthesis of Benzene to tadalafil (Cialis). I am trying to find a link to the detailed mechanism, or at least one that is very close.
Answer:
One wouldn't typically start w/ benzene as a starting material for sildenafil, however, here's a procedure to get you there. The original synthesis of sildenafil was published in Bioorganic & Medicinal Chemistry Letters, Vol 6, pp. 1819, 1824, 1996. The synthetic scheme is listed in the link below.
The benzene intermediate is actually 2-ethoxy benzoylchloride. You would need to make that intermediate from benzene. Perhaps oxidze to phenol, selectively methylate, oxidize that methyl group to the benzoic acid, make the ethoxy ether at the phenol OH, then treat w/ thionly chloride to make the acid chloride intermediate.
That's a lot of work to start at benzene...
Source(s):
http://www.ch.ic.ac.uk/local/projects/p_…
Convert Benzene to Sildenafil Citrate?
Question:
As a bonus for my Organic Class, I am looking for a detailed mechanism for the synthesis of Benzene to Sildenafil Citrate (Viagra) or the synthesis of Benzene to tadalafil (Cialis). I am trying to find a link to the detailed mechanism, or at least one that is very close.
Answer:
One wouldn't typically start w/ benzene as a starting material for sildenafil, however, here's a procedure to get you there. The original synthesis of sildenafil was published in Bioorganic & Medicinal Chemistry Letters, Vol 6, pp. 1819, 1824, 1996. The synthetic scheme is listed in the link below.
The benzene intermediate is actually 2-ethoxy benzoylchloride. You would need to make that intermediate from benzene. Perhaps oxidze to phenol, selectively methylate, oxidize that methyl group to the benzoic acid, make the ethoxy ether at the phenol OH, then treat w/ thionly chloride to make the acid chloride intermediate.
That's a lot of work to start at benzene...
Source(s):
http://www.ch.ic.ac.uk/local/projects/p_…