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Topic: Reaction of drug compound with aqueous acid  (Read 741 times)

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Offline unofku

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Reaction of drug compound with aqueous acid
« on: May 14, 2020, 12:08:59 PM »
I was given the drug compound (s)-Fluoxetine FC(F)(C1=CC=C(O[C@@H](CCNC)C2=CC=CC=C2)C=C1)F

and among other things I should figure out how it reacts in aqueous acid. However, this is a bit difficult for me. I am thinking that it is the 2° Amine that is most likely to react, but I dont know how.
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Offline AWK

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Re: Reaction of drug compound with aqueous acid
« Reply #1 on: May 14, 2020, 12:17:26 PM »
And how does ammonia react with acid? Amine is a derivative of ammonia.
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Offline unofku

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Re: Reaction of drug compound with aqueous acid
« Reply #2 on: May 14, 2020, 12:31:40 PM »
It would become protonated NH2+ as well as form water ?

And this would be the compound FC(F)(C1=CC=C(O[C@@H](CC[NH2+]C)C2=CC=CC=C2)C=C1)F

It just seems too simple to be correct, but maybe I am overthinking it
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Offline AWK

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Re: Reaction of drug compound with aqueous acid
« Reply #3 on: May 14, 2020, 12:56:05 PM »
Many things in chemistry are just as simple.
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Offline rolnor

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Re: Reaction of drug compound with aqueous acid
« Reply #4 on: May 14, 2020, 01:18:40 PM »
Its possible to hydrolyze the benzyl ether bond if you use a strong acid like hydrobromic acid at reflux.
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