The next experimental case study features the transformation of the starting material, 23, into the NK1 receptor antagonist intermediate, 24, as shown in Scheme 6. In this optimization campaign, the MTBO algorithm leveraged data from the previous three case studies, yet this is the first substrate that forms a 6-membered cyclized ring instead of the typical 5-membered ring in the previous oxindoles. Initial experiments in previously identified well-performing parameter space produced low yields, but the algorithm could thereby determine that further exploration of the parameter space was important as the substrate showed more variability from the previous tasks.