how to remove apostrophes that contain a word?

Let's say I have a list that goes something like:

list = [" I wish I was Alex's best 'friend' "]

I want to remove the apostrophe that contains friend but not the apostrophe that is used in Alex's, If I try this with re.sub like so:

list = re.sub('\'\')', '', list)

it removes all the apostrophes which I don't want, how can I achieve this so that the result is:

list = [" I wish I was Alex's best friend " ]

Another way of doing it:

re.sub(r"(?<![a-zA-Z])'(.*?)'(?![a-zA-Z])", r'', list[0])

This looks for an apostrophe, followed by anything, followed by another apostrophe, as long as there isn't a letter just before the first apostrophe or just after the last one.

Assuming apostrophes are only around a single word at a time and not a full sentence, you can use this:

re.sub(r"'(\w+)'", "", your_string)
# your_string can be strings from your list if you iterate over it

This will catch words surrounded by apostrophes, and remove these apostrophes. Therefore, if there's only a single apostrophes as in Alex's or it's, it won't remove them.

Please be aware this will not always work, for example if there are apostrophes around Alex's, there's no way to know which apostrophe to remove (there is, but it wouldn't be handled by this regex)

Update

You can make use of a greedy (> 0) quantifier and an alternate statement in order to remove apostrophes around Alex's:

re.sub(r"'((?:\w|')+)'", "\1", your_string)