Trifluoroacetic acid → HCID 121480767, compound

Participants

Reaction Steps

A solution of tert-butyl((R)-3-hydroxy-1-(((1R,3S)-3-((3-methyl-8-((R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)quinoxalin-2-yl)amino)cyclohexyl)amino)-1-oxopropan-2-yl)carbamate (491, 34 mg, 0.059 mmol) and TFA (0.45 mL, 5.89 mmol) in DCM (0.29 mL) was stirred at 0° C. to RT for 15 min. It was concentrated under reduced pressure. The crude product was dissolved in methanol and injected (3×1 mL) onto the Shimadzu preparative LC (Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 100% over 12 min) before the pure fractions were combined and concentrated via rotary evaporation to give (R)-2-amino-3-hydroxy-N-((1R,3S)-3-((3-methyl-8-((R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)quinoxalin-2-yl)amino)cyclohexyl)propanamide 2,2,2-trifluoroacetate (497, 34 mg, 0.057 mmol, 98% yield) as a red oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18-1.28 (m, 1H) 1.29-1.39 (m, 1H) 1.43-1.52 (m, 2H) 1.45 (d, J=6.65 Hz, 3H) 1.86 (d, J=10.56 Hz, 2H) 2.06-2.15 (m, 2H) 2.53 (s, 3H) 3.55-3.64 (m, 1H) 3.65-3.80 (m, 3H) 4.13-4.26 (m, 1H) 4.55 (q, J=6.85 Hz, 1H) 6.90 (d, J=8.02 Hz, 1H) 6.96 (d, J=1.37 Hz, 1H) 7.33 (t, J=7.73 Hz, 1H) 7.57-7.64 (m, 2H) 7.84 (d, J=7.43 Hz, 1H) 8.00-8.10 (m, 3H) 8.36 (d, J=7.82 Hz, 1H) 11.94 (s, 1H). MS (ESI, pos. ion) m/z: 478.1 (M+1).

Provenance & Evidence