Yesterday
Me: cleaves Boc group to make a primary in methanolic HCl
Also me: forgets that there is a ketone in the compound
Today: I looked at the TLC and went "uh oh". Clean-ish conversion to a single much higher Rf spot (I was thinking if I got imine formation it would just be a polymeric mess). So I drew some stuff in chemdraw and lo-and-behold it's possible to make a 15 member macrocycle if I draw an intra molecular imine bond. Dammit. Odds of my breaking that to rescue the 95 mg of material in here without also cleaving one of the multiple amide bonds doesn't look good (10 min with 2 M aqueous HCl at room temp certainly didn't do it).
NMR is a bit messy, but the chemical shift for the 1H that might tell me what happened (I didn't put enough in the tube to resolve the 13C carbonyls, whoops) looks more like imine adjacent than amine adjacent.
Might just have to put more sample in the NMR tube to prove I screwed up?