HCID 118574928, compound → LSZ-102

Participants

Reaction Steps

To a solution of (E)-methyl 3-(4-((2-(2-(1,1-difluoroethyl)-4-fluorophenyl)-6-hydroxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (1.4 g, 2.89) in THF (5 mL) and water (3 mL) was added 56% LiOH monohydrate (371 mg, 8.67 mmol). The resulting mixture was stirred at room temperature for 18 h after which time the reaction was concentrated in vacuo to remove THF and the resulting solution was diluted with water and acidified by addition of HCl (1N aq.), causing a precipitate to crash out. The resulting precipitate was filtered to give (E)-3-(4-((2-(2-(1,1-difluoroethyl)-4-fluorophenyl)-6-hydroxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid as a white solid which was not purified further (980 mg, 2.021 mmol, 69.9% yield). 1H NMR (400 MHz, CD3OD) δ ppm=1.80 (t, J=18.44 Hz, 3 H), 6.23 (d, J=16.17 Hz, 1 H), 6.71-6.81 (m, 3 H), 7.03 (td, J=8.21, 2.78 Hz, 1 H), 7.08-7.14 (m, 2 H), 7.22-7.32 (m, 2 H), 7.37 (d, J=8.59 Hz, 2 H), 7.47 (d, J=16.17 Hz, 1 H), LC/MS (m/z, M−H): 468.9.

Provenance & Evidence