Water → HCID 54588114, compound

Participants

Reaction Steps

A solution of 0.017 g (0.026 mmol) of tert-butyl(2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazo-6-yl}methyl)pyrrolidine-1-carboxylate from Step B above in 2 mL of a 3:3:1 trifluoroacetic acid:acetonitrile:water mixture was stirred at 70° C. for 3 h. All volatiles were removed in vacuo and the crude light brown residue was purified by reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to afford the title compound as a white solid. 1H-NMR (500 MHz, CD3OD) δ 8.85-8.62 (m, 1H), 8.57-8.31 (m, 1H), 7.91-7.65 (m, 2H), 7.64-7.24 (m, 9H), 6.86-6.59 (m, 1H), 6.19-5.87 (m, 1H), 4.85-4.67 (m, 2H), 4.04-3.68 (m, 4H), 3.28-3.10 (m, 2H), 2.30-1.62 (m, 4H). LC/MS: m/z (ES) 430.2 (MH)+.

Provenance & Evidence