Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

tert-Butyl(R)-1-(4-(furan-3-yl)phenyl)-4-((R)-3-(1-(3-methoxypropyl)-1,1-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (54A) was dissolved in 25% trifluoroacetic acid and stirred at room temperature for 3 hrs. Solvent was removed under vacuum and purified by preparatory LC/MS (20-50% CH3CN in H2O) to give product (R)-3-amino-4-(4-(furan-3-yl)phenyl)-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one (145) as a TFA salt (32 mg, 64% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (br. s., 1H) 1.72-2.22 (m, 5H) 2.57-3.51 (m, 1H) 3.71 (br. s., 1H) 3.77-4.73 (m, 5H) 6.96 (br. s., 1H) 7.30 (m, 2H) 7.37-7.50 (m, 2H) 7.59 (m, 2H) 7.75 (br. s., 3H) 8.17 (s, 1H). ESI-MS:mlz 501.2 (M+H)+.

Provenance & Evidence