Hi brockman,
Which model Sony is it? PRS-505 or PRS-700?
I'd recommend posting in one of the Calibre forums on this. I seem to remember there were some issues with calibre and Sonys. If all else fails you should be able to get calibre to save the book you've loaded into calibre as a .lrf (via the Output selection). Then plug the Sony into the Mac and it should appear, just as a USB key or disk would. I think you can then copy the file direct onto the Sont and it will all work. (But I don't have a mac..)
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