Operation not permitted error while trying to install pip modules - python-2.7

Question

I am getting the below error while trying to install retrying module via pip.
The directory '/Users/ppious/Library/Caches/pip/http' or its parent directory is not owned by the current user and the cache has been disabled. Please check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
The directory '/Users/ppious/Library/Caches/pip' or its parent directory is not owned by the current user and caching wheels has been disabled. check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
Collecting retrying
Downloading retrying-1.3.3.tar.gz
Collecting six>=1.7.0 (from retrying)
Downloading six-1.10.0-py2.py3-none-any.whl
Installing collected packages: six, retrying
Found existing installation: six 1.4.1
DEPRECATION: Uninstalling a distutils installed project (six) has been deprecated and will be removed in a future version. This is due to the fact that uninstalling a distutils project will only partially uninstall the project.
Uninstalling six-1.4.1:
Exception:
Traceback (most recent call last):
File "/Library/Python/2.7/site-packages/pip-8.1.2-py2.7.egg/pip/basecommand.py", line 215, in main
status = self.run(options, args)
File "/Library/Python/2.7/site-packages/pip-8.1.2-py2.7.egg/pip/commands/install.py", line 317, in run
prefix=options.prefix_path,
File "/Library/Python/2.7/site-packages/pip-8.1.2-py2.7.egg/pip/req/req_set.py", line 736, in install
requirement.uninstall(auto_confirm=True)
File "/Library/Python/2.7/site-packages/pip-8.1.2-py2.7.egg/pip/req/req_install.py", line 742, in uninstall
paths_to_remove.remove(auto_confirm)
File "/Library/Python/2.7/site-packages/pip-8.1.2-py2.7.egg/pip/req/req_uninstall.py", line 115, in remove
renames(path, new_path)
File "/Library/Python/2.7/site-packages/pip-8.1.2-py2.7.egg/pip/utils/__init__.py", line 267, in renames
shutil.move(old, new)
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 302, in move
copy2(src, real_dst)
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 131, in copy2
copystat(src, dst)
File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 103, in copystat
os.chflags(dst, st.st_flags)
OSError: [Errno 1] Operation not permitted: '/tmp/pip-ugYqQT-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/six-1.4.1-py2.7.egg-info'
You are using pip version 8.1.2, however version 9.0.1 is available.
You should consider upgrading via the 'pip install --upgrade pip' command.
I am using Mac OSX El Capitan. The error says OSError: [Errno 1] Operation not permitted. I tried running the same command with sudo and the error message is still there.

Answer 1

El Capitan comes with an older version of six installed which cannot be modified. Pip is trying to uninstall it as part of an upgrade and cannot do that. Try this:
pip install retrying --ignore-installed six
Ideally you would use a virtualenv which will allow you to install all the required versions.