RE: ORGLIST: amine protection

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From: Thomas Høeg-Jensen (TSHJ$##$NOVO.dk)
Date: Wed Sep 27 2000 - 11:34:18 EDT

Of several labile amides that come to mind, I will mention the indoline
amide.
Indolinides can be oxidized by DDQ to the indole amides, which cleaves
mildly, e.g. with LiOH at room temperature.
DDQ is dichlorodicyanoquinone. It is in older litterature, but KC Nicolaou
used it very recently for synthesis of a CP molecule, as described in Ang.
Chem.
Personally, I used the method recently for an amino acid protection and
found it to work well.

Thomas Hoeg-Jensen, Denmark

-----Original Message-----
From: owner-orglist$##$dq.fct.unl.pt [mailto:owner-orglist$##$dq.fct.unl.pt]On
Behalf Of César Barbero
Sent: 27. september 2000 15:22
To: Multiple recipients of list orglist
Subject: ORGLIST: amine protection

Dear people,
I'm trying to protect a secondary amino(diphenylamine) group in a
molecule using the formation of an amide. The protection step (reaction
with 10% acetic anhidride in acetic acid and a drop of concentrated
sulfuric acid) works very well but after the intended reaction we are
unable to hydrolize the amide. We hace tried with 10 % KOH in water and
ethanol, 10% sulfuric and HCl, CO3K2 in CH3OH, t-ButO- in tButOH
without sucess. Any suggestions? (other than to change the protecting
group).
Thank you in advance

Dr. Cesar Barbero

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