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Topic: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine  (Read 3819 times)

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reesew

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Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine
« 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!!!!!!!!!!!!!
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Offline Will

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Re: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine
« Reply #1 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').
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Offline Will

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Re: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillamine
« Reply #2 on: May 10, 2006, 06:14:12 PM »
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Offline AWK

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Re: Synthesize N-acetyl D,L-penicillamine into S-nitroso-N-acetyl D,L-penicillam
« Reply #3 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.
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