Water → HCID 71494738, compound

Participants

Reaction Steps

(Z)-methyl 1-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)azetidine-3-carboxylate (0.1 g, 1.0 eq.) was dissolved in methanol:water (10 mL, 1:1). LiOH (0.010 g, 1.0 eq.) was added. The reaction mixture was stirred at room temperature for 1-2 h. The reaction mixture was quenched with 10 mL water and acidified with dilute HCl until pH=2-3. The aqueous layer was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford 0.060 g of (Z)-1-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)azetidine-3-carboxylic acid (62.5% yield). 1H NMR (400 MHz, DMSO) δ=9.38 (s, 1H), 8.54 (s, 2H), 8.29 (s, 1H), 7.40-7.42 (d, J=10.4 Hz, 1H), 5.93-5.96 (d, J=10.4 Hz, 1H), 4.23-4.27 (m, 2H), 4.12-4.16 (m, 3H). LCMS calcd. for C17H13F6N4O3 [M+H]+: 435.29. Found: 435.14, at 2.55 min retention time.

Provenance & Evidence