re = /(?<=CHEM|HIST)\s*|(?<=MATHS)\s*/m
str = 'CLASS 8B CHEM | MON | 10AM to 10:40AM
--Rescheduled-- CLASS 8B MATHS | MON | 11AM to 11:40AM
CLASS 8B HIST | MON | 5PM to 5:40PM\'
CLASS 8B CHEM | MON | 10AM to 10:40AM
'
subst = '<A-WHITE-SPACE>'
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