Sodium Hydroxide → 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoic acid

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Reaction Conditions

Reaction Steps

D3 (600 mg) was treated with 2 M aq. NaOH (25 ml) and MeOH (25 ml). This mixture was stirred overnight then heated to 50° C. for 6 hours. The MeOH was then evaporated and the remaining solution acidified and extracted with EtOAc (×3). The combined organic solutions were washed with brine and evaporated to give the crude residue C(302 mg) as an off-white solid. This was triturated with cold MeOH to give the title compound (162 mg) as a grey solid. δH (d6-DMSO, 400 MHz): 2.80 (2H, t), 4.46 (2H, t), 6.64 (1H, d), 7.49-7.59 (6H, m), 7.72 (1H, d), 7.85 (1H, dd), 8.22-8.25 (1H, m), 8.31-8.34 (1H, m). MS (ES): C24H16F3N3O3S requires 483; found 484 (MH+).

Provenance & Evidence