Nothing off the top of my head for "recent" cases from big tech companies (I'm sure there are smaller companies), but in 2015 Paypal got hit by the Office of Foreign Assets Control.
As for export laws, in 2017 there was 31 individuals and businesses convicted resulting in $287,102,532 in criminal fines, $166,234,123 in forfeitures & 576 months of imprisonment And 52 administrative cases resulting $692,296,500 in administrative penalties.