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. Author manuscript; available in PMC: 2014 May 23.
Published in final edited form as: J Med Chem. 2013 May 13;56(10):4028–4043. doi: 10.1021/jm400241j

Scheme 1.

Scheme 1

General procedure for the synthesis of benzoxazole derivatives.

Reagents and conditions: (a) R1-CHO, O2, DarcoKB, xylene, 120 °C, 6 h, 70–80% (b) H2 (1 atm), 10% Pd-C, EtOAc, 6 h, 80–86% (c) R3CHBrCOOR4, K2CO3, DMF, rt, 5 h, 85–92% when Y = O (or 70 °C, 3 h, 36% when Y = NH) (d) (R)- or (S)- R3CH(OH)COOR4, 0 °C, PPh3, 10 min, DEAD, rt, 12 h, 75–84% (e) 3 M NaOH, THF:H2O (2:1), 80 °C, 3 h, 85–95% (f) 3N HCl, THF, 70 °C, 6 h, 60–70% (g) EDCI•HCl, DMF, 0 °C - rt, 12 h, 63–79% (h) MeI, NaH, THF, 0 °C - rt, 1.5 h, 48%.