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Author: Subject: Warfarin syntheses
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[*] posted on 26-4-2023 at 11:47


Quote: Originally posted by Mateo_swe  

I have seen what Warfarin does to rats, it doesnt seem nice at all, there must be better ways.


Really? Pray tell, how and when did you see this?
A warfarin overdose should most likely result in gastrointestinal bleeding. The gut of mammals has a HUGE, extremely vasculated surface area, and bleeding disorders generally start there. To sieve blood into the gut is a pretty painless thing, you get tired, drowsy, shot of breath and faint.

Or it's a haemorrhage stroke. That can be painful, but not for long. Not like drowning.
Bleeding is sort of painless. So I really wonder what you saw?

And regarding the chemistry I have actually reached a dead end when it comes to the reagents. My hope was there would be a route with affordable and accessible precursors, but I still haven't found one.

[Edited on 20232323/4/26 by DocX]
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[*] posted on 28-5-2023 at 12:47


Reviving the thread. Did anyone succeed in 4-hydroxycoumarin synthesis?
Here I found a German page with coumarin synthesis:
http://forum.lambdasyn.org/index.php/topic,1471.0.html
I synthesized the second reactant (benzylideneacetone) here:
https://www.sciencemadness.org/whisper/viewthread.php?tid=15...
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[*] posted on 10-10-2023 at 06:27


This seems to be a suitable home lab way for warfarin. But only racemic product. For obtaining stereoisomers it would be necessary to have (R,R)- or (S,S)-1,2-diphenylethylenediamine:
https://pubs.acs.org/doi/10.1021/ed800040m

Benzalacetone synthesis is here:
https://www.sciencemadness.org/whisper/viewthread.php?tid=15...

The 4-hydroxycoumarin may be obtained from phenol and meldrum acid:

Quote:
Treatment of phenol with meldrum acid under solvent-free condition at 90°C afforded 3-oxo-3-phenoxypropanoic acid in 92% isolated yield, that transformed to 4-hydroxycoumarin in 75 % and 48% isolated yield, upon treatment with Eaton’s reagent or polyphosphoric acid (PPA)


Attachment: j.arabjc.2015.06.012.pdf (1.6MB)
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The meldrum acid may be obtained by reacting malonic acid + acetone + acetic anhydride + cat. H2SO4

Attachment: CT9089300598.pdf (244kB)
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