re = /\s*-\s*(\(\d{5}\))\s*-\s*(\w{3}\s\d{4}\w?-\d{3}-(?:[^.\s]|\b\s\b)+)\s*-\s*([^.]+\.txt)$/m
str = '201308 - (82608) - MAC 2233-007-Methods of Calculus - Klingler, Lee.txt
201308 - (12345) - ABC 2233L-007-course Name 1 - last, first.txt
@ @ @ @ @ @ 123 abc - a-1 - b-2.txt
201308-(82609) -MAC 2233-007-Methods of Calculus - Klingler, Lee.txt
201308 - (12345)-ABC 2233L-007-course Name-last, first.txt
201308-(12345)-ABC 2233L-007-course Name-last, first.txt'
subst = ' - \\1 - \\2 - \\3'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html