Acetic Acid → HCID 46853081, compound

Participants

Reaction Steps

A solution of LiOH (2.0 M in water, 4.5 mL, 9.0 mmol) was added to a solution of ethyl N-(4-{(1S)-1-[(5-chloro-7-cyano-1-benzothien-3-yl)(4-chlorophenyl)methyl]butyl}benzoyl)-β-alaninate (0.100 g, 0.168 mmol) in THF (9.0 mL). The mixture was stirred at room temperature for four hours then acidified with acetic acid and extracted with ethyl acetate. The organics were dried over Na2SO4, filtered, then concentrated. The resulting residue was purified by reverse-phase HPLC eluting with 20-100% acetonitrile/water containing 0.1% TFA. Following lyophilization, the material was further purified by silica gel chromatography eluting with 5% MeOH in DCM containing 0.5% acetic acid to afford the title compound as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.77 (br s, 1H); 7.60 (d, J=5 Hz, 2H); 7.52 (br s, 1H); 7.42 (br s, 1H); 7.31-7.35 (m, 4H); 7.25 (d, J=7 Hz, 2H); 6.78 (br s, 1H); 4.49 (d, J=11 Hz, 1H); 3.67 (br s, 2H); 3.44-3.47 (m, 1H); 2.66 (br, 2H); 1.45-1.53 (m, 2H); 0.98-1.05 (m, 2H); 0.73 (t, J=7 Hz, 3H). LC1: 3.97 min. (M+H)+ 565.

Provenance & Evidence