Diisopropylethylamine → HCID 59852617, compound

Participants

Reaction Steps

4-Hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2(4′-methanesulfonyl-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (49 mg) was prepared from acetic acid 3-chlorocarbonyl-4′-trifluoromethyl-biphenyl-4-yl ester (1.93 mL, 0.1 M CH2Cl2) and 2-(4′-methanesulfonyl-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethylamine hydrochloride (80 mg, 0.175 mmol) and DIEA (92 μL, 0.525 mmol) using standard procedure M. The crude reaction mixture was concentrated and redissolved in THF (3 mL) and MeOH (1 mL). 1 N NaHCO3 (200 μL) and 1N Na2CO3 (50 μL) were added and the hydrolysis was followed by TLC and LCMS. Once complete, the reaction was diluted with EtOAc and the layers were separated. After extraction and drying the combined organics over MgSO4, the crude mixture was concentrated onto silica gel and purified by chromatography using 15% EtOAc in hexanes.

Provenance & Evidence