Trifluoroacetic acid → 3-{2-{[(2,5-Dichloro-thiophene-3-carbonyl)-methyl-amino]-methyl}-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid

Participants

Reaction Steps

A solution of 3-{2-{[(2,5-dichloro-thiophene-3-carbonyl)-methyl-amino]-methyl}-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid tert butyl ester (50 mg, 0.079 mmol) in CH2Cl2 (2 mL) was treated with anisole (1.0 mL) then TFA (0.6 mL). The solution was stirred at ambient temperature 2 h, and more TFA (1.0 mL) was added. After 15 min, the reaction was concentrated and co-evaporated with CCl4 (3×). The residue was triturated with hexanes to yield a foam (43 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 2.36 (s, 3H), 2.48 (t, 0.6H, J=7.8 Hz), 2.58 (t, 1.4H, J=7.8 Hz), 2.72 (t, 0.6H, J=7.8 Hz), 2.84 (s, 2H), 2.90 (t, 1.4H, J=7.8 Hz), 2.93 (s, 1H), 2.98 (brs, 2H), 4.17 (t, 2H, J=6.4 Hz), 4.47 (s, 0.6H), 4.71 (s, 1.4H), 6.61 (brs, 0.3H), 6.71-6.76 (m, 2H), 6.79 (s, 0.7H), 7.04 (d, 0.3H, J=8.3 Hz), 7.08 (d, 0.7H, J=8.3 Hz), 7.41-7.43 (m, 3H), 7.94 (brs, 2H).

Provenance & Evidence