Dichloromethane → HCID 59704211, compound

Participants

Reaction Steps

To an oven-dried one-neck round bottom reaction flask charged with a magnetic stir bar at rt under argon was added (9H-fluoren-9-yl)methyl((R)-2,8-diamino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-4H-chromen-7-ylcarbamoyl)methylcarbamate (0.050 g, 0.072 mmol), CH2Cl2:MeOH, 1:1 (2.40 mL) and 2N NaOH (0.072 mL, 0.14 mmol). The orange suspension was stirred at rt 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, gradient elution with CH2Cl2:MeOH, 96:4 to 90:10 with trace Et3N) gave 0.012 g (35%) of the title compound as a yellow solid: 1H-NMR (CDCl3): 9.34 (br s, 1H), 6.90 (d, J=1.9 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 6.71 (d, J=1.9 Hz, 1H), 6.37 (d, J=8.2 Hz, 1H), 4.72 (br s, 2H), 4.64 (s, 1H), 4.29 (br s, 2H), 3.84 (s, 3H), 3.83 (s, 3H), 3.54 (br s, 2H).

Provenance & Evidence