[LauraAnne]

I'm trying to couple a carboxylic acid to an amine in DMF using PyBOP.  The molecule I'm using also has sulfonate groups on it, however, and I'm a little concerned they will react with the PyBOP and amine in some funky way.  (I'm not much of an organic chemist).   I haven't been able to find an example where this has happened searching online and I know that the PyBOP acts by creating an ester.  I've also learned that this coupling can be done with Woodwards reagent, which itself contains a sulfonate.  So I think I'm ok, but the doubts are a little nagging still, so I thought I'd ask . . . . figured it couldn't hurt

[movies]

If the stuff you are using isn't too valuable, I would just try it on small scale and see what you get.  It might not be a problem.

I would expect acids to react faster than sulfonates.  Does your sulfonate have a free OH?