This will not work the way you are thinking. WordPress will try to upload attachments (images, pdfs, etc) to your server using the UPLOADS constant, this path is a file path, local to the server.
If you wish to use a CDN you can get a CDN service to do this (manage files and upload them remotely to their service) or possibly use a tool like this to rewrite URLs on the fly.
I can’t say how good this plugin is but seems like this could do what you are looking for, upload your attachments to another (remote) server.
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