Dichloromethane → HCID 59704203, compound

Participants

Reaction Steps

To an oven-dried one-neck round bottom reaction flask charged with a magnetic stir bar at room temperature under argon was added (9H-fluoren-9-yl)methyl(S)-1-((R)-2,8-diamino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromen-7-ylcarbamoyl)-ethylcarbamate (0.045 g, 0.063 mmol), CH2Cl2:MeOH, 1:1 (2.11 mL) and 2N NaOH (0.063 mL, 0.13 mmol). The orange suspension was stirred at room temperature overnight. The suspension was concentrated leaving a brown residue. The residue was extracted with CHCl3 (3×40 mL), dried over MgSO4, filtered and concentrated to give the crude product. Purification by flash column chromatography (silica gel 4 g pre-packed column, elution with CH2Cl2:MeOH, 1:1) gave 0.005 g (16%) of the title compound as a yellow solid: 1H-NMR (DMSO-d6): δ 8.32 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.98 (d, J=1.9 Hz, 1H), 6.91 (br s, 2H), 6.86 (d, J=1.9 Hz, 1H), 6.33 (d, J=8.5 Hz, 1H), 4.78 (br s, 2H), 4.69 (s, 1H), 3.80 (s, 3H), 3.70 (s, 3H), 1.22 (d, J=6.9 Hz, 3H). ESI-MS (C21H22BrN5O4) 487.09 m/z (%): 488 [M+H]+ (100%), 490 [M+H]+ (90%).

Provenance & Evidence