Reconfigurable computing has the potential for providing significant performance increases to a number of computing applications. However, realizing these benefits requires digital design experience and knowledge of hardware description languages (HDLs). While a number of tools have focused on translation of high-level languages (HLLs) to HDLs, the tools do not always create optimized digital designs that are competitive with hand-coded solutions. This work describes an automatic optimization in the C-to-HDL transformation that reorganizes operations between pipeline stages in order to reduce critical path lengths. The effects of this optimization are examined on the MD5, SHA-1, and Smith-Waterman algorithms. Results show that the optimization results in performance gains of 13%-37% and that the automatically-generated implementations perform comparably to hand-coded implementations.