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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: bapab on February 15, 2017, 11:01:51 PM

Title: Can someone help me to predict what would be the product of this reaction ?
Post by: bapab on February 15, 2017, 11:01:51 PM

Hi

When mixing these 2 compounds (equimolar) in DMSO nothing much happens. But when I add 10N NaOH, the coloration changes to a strong "fluorescent yellow" and a precipitate is formed that slowly turns green. By HPLC a new product appear as well within that precipitate.

Is there any chance that the drug on the left got conjugated to the amino acid on the right ?

thanks ! :)

Title: Re: Can someone help me to predict what would be the product of this reaction ?
Post by: hypervalent_iodine on February 15, 2017, 11:15:19 PM

Two things.

1. The basic compound on the left is incorrect. The COO- you've written in should simply be O-.

2. Do you happen to know the pKa of the phenolic OH? My guess is that you've deprotonated that.

Title: Re: Can someone help me to predict what would be the product of this reaction ?
Post by: bapab on February 16, 2017, 03:29:24 AM

You're right, sorry for the mistakes, the alcohol on the phenol should be deprotonated and my carboxylic acid form also should be as you mentioned.
So no chance that the glutamate got conjugated under these conditions ?
Since I m not a chemist, if anyone would know how to conjugate these 2 that would be helpful !

Thanks !