Sodium Hydroxide → 5-Propylcarbamoyl-biphenyl-3-carboxylic acid

Participants

Reaction Steps

A solution of NaOH (44 mg, 1.1 mmol) in 372 μL of MeOH was added to a solution of 68D (284 mg, 0.96 mmol) in 1.8 mL of acetone. The reaction was stirred at room temperature for 16 hrs after which time 10 mg of NaOH and 200 μL of MeOH were added. The reaction was stirred for 72 hrs. The reaction mixture was then concentrated in vacuo and the residue obtained was dissolved in water and a few drops of concentrated HCl were added till pH ˜1. An off-white solid appeared. It was collected by filtration and extensively rinsed with water. The solid was then dried in vacuo (194 mg, 72%). NMR 1H (ppm, CD3OD): 8.43 (t., J4=1.63 Hz, 1H), 8.38 (t., J4=1.73 Hz, 1H), 8.27 (t., J4=1.78 Hz, 1H), 7.71-7.67 (m, 2H), 7.48 (m, 2H), 7.39 (t.t., J3=7.34 Hz, J4=1.36 Hz 1H), 3.39-3.34 (m, 2H), 1.65 (sext., J3=7.18 Hz, 2H), 0.98 (t., J3=7.34 Hz, 3H).

Provenance & Evidence