Trifluoroacetic acid → alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclopentaneacetic acid

Participants

Reaction Steps

To 26.5 mg of α-(R)-(3-(S)-((4-benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-phenyl-pyrrolidin-1-yl)- cyclohexaneacetic acid, 4-methoxy-benzyl ester (from Step D) was added 0.2 mL of anisole and 2 mL of TFA. After stirring at room temperature for 1.5 hours, concentrated under pressure. The residue was purified by flash chromatography eluting with 10% CH3OH in CH2Cl2, then 15% CH3OH/1% NH4OH in CH2Cl2 to give 24 mg of the title compound as a solid. 1H NMR (400 MHz, CDCl3): δ1.17-3.73 (m, 28H), 4.35 (m, 1H), 7.27 (m, 3H), 7.46(m, 4H), 7.55(s. 1H). 7.65(d, J=7.4 Hz, 1H), 8.17(d, J=5.0 Hz, 1H). ESI-MS 510 (M+H); HPLC A: 1.67 min.

Provenance & Evidence