Triflic Acid
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Catalyst for Amide hydrolysis
Around 7 months ago I tried to produce vanillyl amine from capsaicin. That ended badly because I had trouble finding a good source of capsaicin. Then
I got a position as a chemist and stopped home chemistry altogether to focus on work. Now, I want to try that again, having found a good source of
capsaicin powder. However, from the last attempt, I know that my strategy of boiling it in HCl isn't too effective. I was wondering if anyone knew of
any good catalysts for amide hydrolysis. I did see some data about using metal salts to stabilize the tetrahedral intermediate, but pretty must
everything was difficult to obtain triflate salts or Niobium oxide. So does anyone have any experience with mild amide hydrolysis?
There wasn't a fire, we just had an uncontrolled rapid oxidation event at the power plant.
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Tsjerk
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Vanillyl amine is very sensitive to heating, even in steam it decomposes. I don't know what happens, maybe it is polymerization, maybe it is
oxidization. But at least it is sensitive. I can't imaging there is a way to hydrolyze the amide without destroying the amine.
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Pumukli
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Boffis did a nice hydrolysis research on DEET years ago. Check his work here in the forum (or in the prepublication section), it may give you food
for thought.
[Edited on 29-4-2022 by Pumukli]
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aab18011
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Quote: Originally posted by Triflic Acid  | | Around 7 months ago I tried to produce vanillyl amine from capsaicin. That ended badly because I had trouble finding a good source of capsaicin. Then
I got a position as a chemist and stopped home chemistry altogether to focus on work. Now, I want to try that again, having found a good source of
capsaicin powder. However, from the last attempt, I know that my strategy of boiling it in HCl isn't too effective. I was wondering if anyone knew of
any good catalysts for amide hydrolysis. I did see some data about using metal salts to stabilize the tetrahedral intermediate, but pretty must
everything was difficult to obtain triflate salts or Niobium oxide. So does anyone have any experience with mild amide hydrolysis?
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https://www.nature.com/articles/s41467-020-17588-5
This shows some interesting methods.
Hope it helps
I am the one who boils to dryness, fear me...
H He Li B C(12,14) Na S Cl Mn Fe Cu Zn Ba Ag Sn I U(238)
"I'd rather die on my feet than live on my knees" -Emiliano Zapata
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AvBaeyer
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There is a known method for the "gentle" hydrolysis of an amide in order to isolate the amine portion. This involves the reaction of the amide with
ethylenediamine with a catalyst such as ammonium bromide. The reaction is driven by the formation of an imdazoline from the acid portion of the amide.
The reference is
DOI: 10.1002/anie.201202354 (Angew. Chem. Int. Ed. 2012, 51, 8564 –8567)
AvB
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Triflic Acid
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AvB, thanks, that look pretty intersting. I might give that a try once I can synthesize some ethyldiamine.
There wasn't a fire, we just had an uncontrolled rapid oxidation event at the power plant.
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Fery
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If your goal is just preparing vanillyl amine and not to study the capsaicin hydrolysis itself, then you can try this way:
vanillin + hydroxylamine -> oxime
vanillin oxime + Zn + CH3COOH -> vanillyl amine
https://www.arcjournals.org/pdfs/ijarcs/v5-i10/1.pdf
Attachment: 1.pdf (409kB)
This file has been downloaded 189 times
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Triflic Acid
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I’m actually trying to produce vanillin from capsaicin. So that doesn’t work for me sadly.
There wasn't a fire, we just had an uncontrolled rapid oxidation event at the power plant.
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Dr.Bob
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Using NaOH to cleave amides can work rather than 6N HCl, which is a common method, but requires heating to 60 C or more for many hours. The time and
temp mostly depend on the exact amide/protein being cleaved.
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