Hello,
I have an organic product that is currently stuck in a basic aqueous layer about pH 12-14. I made a mistake and left the "waste" for several months just in case I needed it. Turns out because I misunderstood the chemistry and that my product was push into the aqueous phase when I did this portion of the extraction that it has just been sitting there. Now it is stuck and will not come out with the original method that worked very well when I understood the chemistry and started over. The compound is N-benzyl hydroxy proline methyl ester. Any ideas or pointing me to any papers that would be helpful would be great.
Thanks.
Most probably your (2S,4R)-1-benzyl-4-hydroxyproline methyl ester underwent hydrolysis to (2S,4R)-1-Benzyl-4-hydroxyproline. Therefore it is very soluble in basic aqueous solution. If you want isolate (2S,4R)-1-Benzyl-4-hydroxyproline see attachments
First try to neutralize with mild reagent. then add about 20% ethanol and heat it to 60 C, and then let it to stand for 24 hours. you will find your product in the clear solution, some sedimention you will also find. filter and take your product
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