Trying to keep this absent of political boundaries, so this comes with no view at all on where such boundaries lie in reality, in law or in an idealised world, but I think Hebron to Jerusalem is in theory possible, though in reality almost certainly impossible.
This Route is just over the qualifying 42.159km. It is meets the criteria of being inside the core zone (but only just at their extremities) though I think falls just short of the Eastern boundary of Battir in Bayt Jala, but the
core zone map isn't 100% clear, and trying to get a few hundred metres up the road suddenly forces an 8km detour.
However, it forces a big loop to get out of Hebron which adds about 4 km to the total, without that it would comfortably be under the qualifying distance. It looks like the 3557 out of Hebron crosses through several checkpoints and guard posts, so I assume there are practical reasons for the diversion.
However, I think it is technically possible to cover the 4 core zones in under 42.159km by shaving some parts off even if that loop out of Hebron must be kept.