Author Topic: ethyl diazoacetate:- a novel reagent?
Piglet
Member posted 02-07-99 05:54 AM
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Hi! This morning I was lying in the bath, with a bong, a brew (NB USBs: That means a cup of tea in England, not a beer! I'm not quite that bad) and a book. My book was explaining the formation of aromatic diazonium salts. In this case, though, the book also explained how certain primary amines (those with a strongly electron-withdrawing group such as an ester) would yield a primary diazoalkane. EG:
NH2CH2COOCH2CH3 + NaNO2 + dil.HCl ------->
Glycine ethyl ester
N=N=CHCOOCH2CH3
ethyl diazoacetate
Now, could this be applied to ALL the alpha amino-acids? If so, when the ester is cleaved (notice I didn't just say hydrolised), what is going to happen? I wondered if maybe the diazo group would act in the same way as the nitro group in Rhodiums nitroalkane synth? It would then form diazomethane, a useful agent. With other amino acids, one might yield a number of interesting intermediates. Can diazoethane be oxidized to nitroethane? I don't have a clue. My point is that this could be an interesting class of compounds for synthesis.
Anyone?
Piglet
Piglet
Member posted 02-08-99 04:08 AM
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Oh, I should mention that reflux with HCl yields a Cl group. So you can maybe use this to make chloroacetic acid? Handy for making nitromethane and benzodiazepines (amongst other things). Would alanine yield chloropropionic acid and thence nitroethane?
Piglet
