re = /#(?!(?:hashtag|DoNotRemoveThis)\b)[\w-]+(?=(?:\s+#[\w-]+)*\s*$)/i
str = 'Any #hashtag in the middle of the string should NOT be removed regardless of what it is, for example #DoNotRemoveThis #KeepThisHashtag and any hashtag at the end of the string should be removed UNLESS it matches the exeptions in the regex. #deletethis #DoNotRemoveThis #thismustgoaway'
subst = ''
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