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Topic: Which N is more nucleophilic--Amide N or Indole N  (Read 3414 times)

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Offline taurean

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Which N is more nucleophilic--Amide N or Indole N
« on: July 09, 2008, 07:43:07 PM »
Guys! Is N of delta-lactam more nucleophilic or N of indole more nucleophilic towards BOC protection?

I would like to protect only amide N, leaving indole N unprotected.  What are the chances of protecting one in the presence of the other?

Thanks,

Offline bluenote

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Re: Which N is more nucleophilic--Amide N or Indole N
« Reply #1 on: July 09, 2008, 07:52:25 PM »
Review the pka's of each nitrogen.  Pka generally tracks with nucleophilicity.  I'm not really sure why you would really need to protect an amide in the first place????

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