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. 2014 Sep 10;57(22):9259–9291. doi: 10.1021/jm500828f

Scheme 5. Synthesis of 48.

Scheme 5

Reagents and conditions: (a) K2CO3 (2 equiv), CH3CN, 68%. (b) m-CPBA, CH2Cl2. (c) Ac2O, reflux. (d) NaOH(aq), EtOH, reflux, 4 h, 87%. (e) SO3·pyridine, NEt3, DMSO, CHCl3, 16 h, 83%. (f) H2NOH·HCl, NaOAc, CH3OH, reflux, 2 h, 90%. (g) Ac2O, reflux, 94%. (h) H2, 10% Pd–C, CH3OH, 85%. (i) CH3OH, 0.1 M pH 6 buffer, NaHCO3, 75 °C, 48 h, 95%.