Trifluoroacetic acid → 3-((R)-2-Amino-2-phenyl-ethyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-5-[4-(3-nitro-benzyl)-3-oxo-piperazin-1-yl]-1H-pyrimidine-2,4-dione

Participants

Reaction Steps

To a solution of ((R)-2-{3-(2,6-difluoro-benzyl)-4-methyl-5-[4-(3-nitro-benzyl)-3-oxo-piperazin-1-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-1-phenyl-ethyl)-carbamic acid tert-butyl ester (28 mg, 0.0371 mmol) in 1 mL of dichloromethane was added trifluoroacetic acid (0.1 ml, 1.29 mmol) under ice cooling, followed by stirring at room temperature for 2 hrs. The solution was neutralized with sat. NaHCO3, extracted with dichloromethane and concentrated in a vacuum. The residue was purified by column chromatography eluting with a dichloromethane/methanol (20/1) eluent to afford 11 mg of compound 9-1 (45%). 1H NMR (300 MHz, CDCl3) δ 2.42 (3H, s), 2.81 (1H, m), 3.12 (1H, m), 3.30-3.49 (2H, m), 3.72 (1H, m), 4.02-4.22 (3H, m), 4.33 (1H, dd), 4.55 (1H, m), 4.91 (1H, m), 5.23 (2H, dd), 6.92 (2H, t), 7.20-7.37 (6H, m), 7.53 (1H, t), 7.65 (1H, d), 8.13 (1H, s), 8.15 (1H, m).

Provenance & Evidence