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Which N is more nucleophilic--Amide N or Indole N
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Topic: Which N is more nucleophilic--Amide N or Indole N (Read 3521 times)
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taurean
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Which N is more nucleophilic--Amide N or Indole N
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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,
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bluenote
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Re: Which N is more nucleophilic--Amide N or Indole N
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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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Which N is more nucleophilic--Amide N or Indole N