In the "Master Data Programming Guide":
You cannot get using a predicate based on transient properties (although you can use transient properties to filter in memory yourself) .... To summarize, however, if you select directly, you should usually not add predicates based on Objective -C or sort the descriptors for the query to fetch. Instead, you should apply them to the selection results.
Thus, sorting by the calculated value seems impossible. You must pre-compute the sort value and store it as a (non-transitional) attribute in your objects.
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