I tried to synthesize Fmoc-Tyr(trt)-OH and got a solid that was not dissolved in any solvent, even in a different pH (acid or base). I now doubt that it was Fmoc-Tyr(trt)-OTrt and would like to know how I can find its structure. If in fact it was Fmoc-Tyr(trt)-OTrt, how can I remove the Trt group from carboxyl?
if it is Fmoc-Tyr(trt)-OTrt it will not show the COO-H stretching in the IR spectrum. KBr disc or Goldengate can be used to obtain IR spectrum (No need to dissolve it).
Steps/Stages
1.1 R:AcOH, S:CHCl3, S:MeOH
1.2 R:NaOH, S:H2O
2.1 R:F3CCO2H, S:CH2Cl2
2.2 R:NaOH, S:H2O, S:Et2O
Reference
Schaefer W., 1987: Application of the trt and fmoc groups for the protection of polyfunctional alpha amino acids. Liebigs Annalen Der Chemie: 025-1030
Mass and IR will give idea. Try D2O for NMR. It may be sparingly soluble which would be more sufficient for Mass. Acid can not be protected with Fmoc in the presence of amine. Check the equivalent of Fmoc.
Check its solubility in NaHCO3 for free acid group
U can also detect any free COOH by developping your TLC plate with bromocresol (pH indicator) which will show any free carboxylic function as yellow spot on a blue background..
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