Story related and cannot be missed.
This boss fight is at the end of level 6 and it shouldn't give anybody too much trouble. To dodge most/all of Jake's attacks simple run from right to left or vice versa. To hurt Jake you have to wait until he roars or he is lying down stunned and then shoot him as fast at you can. After you hurt him enough, you have to kill his minions to be able to hurt him again. They should drop items to replenish your health which helps out a lot. After a while of repeating this, you will beat him and the achievement will unlock.