What functional groups on #"methotrexate"# promote water solubility?

1 Answer
Jan 20, 2018

Well, let us look at the structure of the beast...

Explanation:

en.wikipedia.org/wiki/Methotrexate

Now lime water is saturated #Ca(OH)_2#... Because methotrexate is a diacid, treatment with such a reagent would give the dicarboxylate salt...the which would have some water solubility..

And, evidently, extraction into base works.... And whether something works or not is the only CRITERION that is assessed when an organic synthesis is considered. There MAY be better ways....but these have yet to be found. Presumably the aqueous extract is reacidified, and the diacid is extracted back into ether, MINUS some impurities. I am no organic chemist, but this is probably a difficult molecule to synthesize...and yet there are evidently efficient ways to synthesize this cheaply.