Why didn't you run 'pkgdb -F'? That would have suggested what package to upgrade or install to fix the problem.
Basically, pear-1.4.11 needs apache=1/3.37_1, but it is not there. Probably it has been updated without portupgrade knowing about it, and the record needs to be changed to the currently instaled version
Specifying -O just tries to go ahead without fixing that up. Who knows what will happen - probably the build will fail because things are not right - and you will have to fix it with pkgdb, like it suggested.
So, when the portupgrade run fails or completes, run pkgdb -F.
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