Before all the injuries and major slumpage this season, I would have said yes in 2013, but he'd have to finish strong this season and have a hell of a contract year (certainly a possibility) to reach 449. But I think the Sox will resign him anyway and he'll break it.
I also think he has an outside chance at 500 should he decide to keep playing another 5-6 years, although those years wont all be for the Sox...