Hi all, I need to cleave the ester in Ethyl 2-amino-1H-imidazole-5-carboxylate to make the carboxylic acid and retrieve the product from solution to use in downstream applications of linking to amines via reductive amination using sodium cyanoborohydrde.

I tried to cleave the ester with 2M equivalents of KOH in 5:1 MeOH:H2O for 1H at 40C. After 1H, i added 20mL H2O to quench and then tried to precipitate my newly made acid by dropping pH to 1, however nothing precipitated out. I then tried to see if any of my product was unreacted by mixing with diethyl ether to see if any of the light brown color would transfer to the ether layer, but again, nothing happened, the ether layer is completely clear. I guess I should just boil off some water and see if it starts to precipitate out? Im not much of a chemist so I just wanted to make sure I havent made any terrible assumptions along the way...

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