Acetic Acid → HCID 11978048, compound

Participants

Reaction Steps

To a solution of methyl 1-[(4-ethyl-5-{5-[4-(2-methoxyphenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methyl]azetidine-3-carboxylate (86 mg, 0.17 mmol) that was obtained in Example 21 (21c) in dioxane (3 ml) was added a 1N aqueous solution of sodium hydroxide (0.51 ml, 0.51 mmol) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, acetic acid (29 μl, 0.51 mmol) was added to the reaction mixture to quench the reaction, and the resulting mixture was evaporated in vacuo. Subsequently, to the residue obtained were added successively methanol (2 ml) and water (1 ml) with stirring, and furthermore a solution of oxalic acid (8 mg, 0.09 mmol) in methanol (0.5 ml) was added, and then the resulting mixture was stirred for 30 minutes. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with a mixed solvent of water and methanol (3:7) and dried in vacuo to afford the title compound (63 mg) in a yield of 69% as a white crystalline solid.

Provenance & Evidence