Now I'm not going to say what time Chuck appears as that is explained in De4th By Toast's guide. I will be explaining on tactics I used to kill him.
Just like the battle with Leon in DR2, you can do 1 of 2 things, you can shoot at him but that will take forever. The 2nd and more practical plan is to lure him into the fences outside of Uranus Zone (teehee) and that will cause him to crash and get his slicecycle stuck in the railings. Now just wail into his back with preferably powerful melee weapons like the Knife Gloves or the Spiked Bat. Continue this process until Chuck is defeated and once you do that, your achievement will unlock.