Lithium Hydroxide → HCID 58449392, compound

Participants

Reaction Steps

To a stirred solution of methyl 5-amino-4′-methylbiphenyl-3-carboxylate (410 mg, 1.7 mmol) in CH2Cl2 (30 mL) and N,N-diisopropylethylamine (0.44 mL, 2.5 mmol) at 0° C. was added 5-bromopentanoyl chloride (370 mg, 1.9 mmol). The mixture was stirred at room temperature overnight and then washed with aq. Na2CO3 solution and brine, dried (Na2SO4), and concentrated. The residue was dissolved in THF (30 mL) and cooled to 0° C. Sodium tert-butoxide (200 mg, 2.0 mmol) was added and the mixture was stirred at room temperature for 3 h. LC-MS indicated the cyclization reaction was complete. MeOH (20 mL) and water (10 mL) were added followed by lithium hydroxide (120 mg, 5.1 mmol). The mixture was stirred at room temperature for another 3 h, and LC-MS indicated the saponification was complete. The mixture was concentrated in vacuo. The residue was treated with water and acidified to pH 2-3 with 1N HCl, extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to afford a white solid. LC-MS: 310.1 [M+1]+.

Provenance & Evidence