Hydrochloric Acid → HCID 11692076, compound

Participants

Reaction Steps

A mixture of methyl 4-[({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)methyl]benzoate (51 mg, 0.0096 mmol), prepared in the previous step, and 1 N NaOH (145 μL, 0.145 mmol) in 10 mL of THF plus 10 mL of methanol, plus 5 mL of water was refluxed under nitrogen. The reaction was monitored by LC/MS. An additional three aliquots of 145 μL of 1 N NaOH were added over approximately three days of reflux. After cooling to room temperature 1 mL of 1 N HCl was added. The solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (44.3 mg, 89%) as a white solid, mp 251-254° C. Elemental Analysis for C33H27NO5. 0.10 H2O Calc'd: C, 76.31; H, 5.28; N, 2.70. Found: C, 72.79; H, 5.11; N, 2.47.

Provenance & Evidence