Trifluoroacetic acid → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(carboxy)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine

Participants

Reaction Steps

To a solution of 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-α-(t-butoxycarbonyl)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 90; 77 mg, 0.108 mmol) in DCM (3 ml) was added at 0° C. TFA (0.75 ml). The reaction mixture was stirred at room temperature for 2 h and 45 min. The solvent was evaporated under reduced pressure and the crude product was purified by preparative HPLC using MeCN and ammonium acetate buffer (40:60 to 50:50) as eluent to give the title compound 60 mg (82%). NMR (500 MHz, CD3OD) 0.75–0.85 (m, 6H), 1.0–1.25 (m, 4H), 1.40–1.64 (m, 4H), 2.75–2.90 (m, 2H), 3.26 (s, 2H), 3.50–3.90 (m, 2H), 4.30–4.41 (m, 2H), 5.43 (s, 1H), 6.99 (t, 1H), 7.05–7.13 (m, 3H), 7.23–7.34 (m, 5H), 7.45 (d, 2H), 7.52 (s, 1H); m/z 658.

Provenance & Evidence