Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: reesew on May 09, 2006, 05:02:25 PM

Title: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine
Post by: reesew on May 09, 2006, 05:02:25 PM
Hi, I'm new to this forum, and would love some help on this problem.

I need to know how to convert N-Acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine (SNAP).

Thanks in advance!!!!!!!!!!!!!
Title: Re: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine
Post by: Will on May 10, 2006, 01:58:36 PM
Hi,

From what I've read, you just add HNO2 (which needs to be made my sodium nitrite with an acid like HCl).

The attatched .pdf says how they did this reaction (first sentence under 'method').
Title: Re: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine
Post by: Will on May 10, 2006, 06:14:12 PM
But this says something else:
http://pubs.acs.org/subscribe/journals/jacsat/suppinfo/ja039466i/ja039466isi20031223_021758.pdf
Title: Re: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillam
Post by: AWK on May 11, 2006, 01:46:37 AM
HNO2 reacts with NH2 group easily, hence you should protect this group before nitrosylation of SH group( choosing a good protecting group is a critical point for success of this synthesis), and protecting group should be removed without decomposition of S-N bond.