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Confirmation of Synthesis: using MS to identify a protective group

Many organic chemists employ Mass spectrometry (MS) as a convenient verification tool for their product in a synthetic reaction. Derivatization such as adding a protective (or protecting) group can often be detected by MS.

The EI mass spectrum for tert-butyl 3-aminopiperidine-1-carboxylate is shown below. The ‘terminal’ atoms belonging to the protective group, tert-Butyloxycarbonyl (BOC or t-BOC), are coloured in blue. Although the parent ion is not clearly evident, the mass spectrum shows 3 ion clusters: m/z 57, 99 and 127 with the¬†associated fragments listed below.



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